Co-reporter:Hai-juan Lv;Xiao-tai Zhang;Shu Wang
Analyst (1876-Present) 2017 vol. 142(Issue 4) pp:603-607
Publication Date(Web):2017/02/13
DOI:10.1039/C6AN02705A
Two BODIPY-carbazole dye based fluorescent probes BCA and BCAS were designed, synthesized and encapsulated by liposomes to obtain fluorescent nanoparticles BCA-FNP and BCAS-FNP. The fluorescence imaging showed that BCA-FNP was membrane-permeable and capable of localizing lysosomes in living cells.
Co-reporter:Xiao-tai Zhang, Guang-jian Liu, Zhang-wei Ning, Guo-wen Xing
Carbohydrate Research 2017 Volume 452(Volume 452) pp:
Publication Date(Web):27 November 2017
DOI:10.1016/j.carres.2017.10.010
•Unimolecular sensors including monoboronic acid and di-/multi-boronic acids were designed for detecting saccharides.•Two-component sensing systems were fabricated for saccharides discrimination.•Assembly-based sensing systems was well explored for saccharides recognition.•Boronic acid-functionalized nanomaterials and surfaces have been achieved for saccharides sensing.During the past decades, the interaction between boronic acids-functionalized sensors and saccharides is of great interest in the frontier domain of the interdiscipline concerning both biology and chemistry. Various boronic acid-based sensing systems have been developed to detect saccharides and corresponding derivatives in vitro as well as in vivo, which embrace unimolecular sensors, two-component sensing ensembles, functional assemblies, and boronic acid-loaded nanomaterials or surfaces. New sensing strategies emerge in endlessly with excellent selectivity and sensitivity. In this review, several typical sensing systems were introduced and some promising examples were highlighted to enable the deep insight of saccharides sensing on the basis of boronic acids.Download high-res image (248KB)Download full-size image
Co-reporter:Cui-yun Li, Guang-jian Liu, Wei Du, Yuan Zhang, Guo-wen Xing
Tetrahedron Letters 2017 Volume 58, Issue 22(Issue 22) pp:
Publication Date(Web):31 May 2017
DOI:10.1016/j.tetlet.2017.04.056
•A new O-fucosylation method promoted by (p-Tol)2SO/Tf2O was reported.•Secondary sugar alcohol acceptors gave high yields and α-stereoselectivities in the fucosylation.•Lewisa was facilely synthesized in nine linear steps with 27% overall yield.Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained with secondary sugar alcohol as acceptors. Moreover, the novel fucosylation strategy was successfully applied to the synthesis of an important Lewis blood group antigen Lewisa, which was obtained in nine linear steps with 27% overall yield.Download high-res image (60KB)Download full-size image
Co-reporter:Qin-chao Xu, Zhen-yuan Gu, Guo-wen Xing
Tetrahedron 2017 Volume 73, Issue 15(Issue 15) pp:
Publication Date(Web):13 April 2017
DOI:10.1016/j.tet.2017.02.060
A novel fluorescent chemosensor HACBA with carbazole-hemicyanine fluorophore as signal reporter and N,N,N'-tri(2-pyridylmethyl)ethylenediamine (TPEA) as binding sites was designed and synthesized. Its assemblies with anionic surfactant sodium dodecyl sulfate (SDS) show improved fluorescence emission stability and enhanced fluorescence intensity. HACBA/SDS system can selectively recognize Cu2+, which led to a dramatic fluorescence quenching. The in situ resultant HACBA-Cu(II)/SDS ensemble functioned as a highly selective and sensitive sensor for H2S with a turn-on fluorescent response. Our results show that the “on-off-on” molecular switch occured through the reversible formation-dissociation reaction between HACBA-Cu(II) complex and HACBA/CuS in the SDS micellar solution, and at least 3 cycles of on-off-on switches were observed.A novel carbazole-hemicyanine hybrid based “on-off-on” molecular switch (HACBA) was designed and synthesized. The surfactant-assisted HACBA-Cu(II)/SDS ensemble were successfully used for selective sensing of H2S.Download high-res image (183KB)Download full-size image
Co-reporter:Xiao-tai Zhang, Shu WangGuo-wen Xing
ACS Applied Materials & Interfaces 2017 Volume 9(Issue 4) pp:
Publication Date(Web):January 10, 2017
DOI:10.1021/acsami.6b13363
Ginsenoside is a large family of triterpenoid saponins from Panax ginseng, which possesses various important biological functions. Due to the very similar structures of these complex glycoconjugates, it is crucial to develop a powerful analytic method to identify ginsenosides qualitatively or quantitatively. We herein report an eight-channel fluorescent sensor array as artificial tongue to achieve the discriminative sensing of ginsenosides. The fluorescent cross-responsive array was constructed by four boronlectins bearing flexible boronic acid moieties (FBAs) with multiple reactive sites and two linear poly(phenylene-ethynylene) (PPEs). An “on-off-on” response pattern was afforded on the basis of superquenching of fluorescent indicator PPEs and an analyte-induced allosteric indicator displacement (AID) process. Most importantly, it was found that the canonical distribution of ginsenoside data points analyzed by linear discriminant analysis (LDA) was highly correlated with the inherent molecular structures of the analytes, and the absence of overlaps among the five point groups reflected the effectiveness of the sensor array in the discrimination process. Almost all of the unknown ginsenoside samples at different concentrations were correctly identified on the basis of the established mathematical model. Our current work provided a general and constructive method to improve the quality assessment and control of ginseng and its extracts, which are useful and helpful for further discriminating other complex glycoconjugate families.Keywords: boronic acid; ginsenosides; pattern recognition; polyelectrolyte; sensor array;
Co-reporter:Xiao-tai Zhang, Shu Wang, and Guo-wen Xing
ACS Applied Materials & Interfaces 2016 Volume 8(Issue 19) pp:12007
Publication Date(Web):April 25, 2016
DOI:10.1021/acsami.6b01940
Four-channel fluorescence assay toward six monosaccharides was achieved by employing two novel pyrene-functionalized boronlectins with flexible diboronic acid as receptors. The effects of pH values and aging time on the sensor properties were thoroughly evaluated by UV–vis, fluorescence spectroscopy and dynamic light scattering. We find that the fluorescence relative ratios were highly correlated with analyte concentrations at μM level. The flexibility of the receptors was perceived as an indispensable factor to produce diverse fluorescence signals toward different monosaccharides. Most importantly, integration of four fluorescence channels derived from the two sensors enables an excellent discrimination for all tested monosaccharides at a certain concentration or a concentration range via linear discriminant analysis (LDA). It is proposed that the multiple flexible linkers in the boronlectins could increase their self-adaptive capacity for different analytes, and facilitate the formation of stable boronlectin–sugar aggregate assemblies. In addition, practical sensing of glucose in the simulative blood and urine was illustrated to be feasible in the presence of interferences at physiological concentrations.Keywords: aggregates; boronlectin; monosaccharide; pyrene; sensor
Co-reporter:Guang-Jian Liu, Zi Long, Hai-juan Lv, Cui-yun Li and Guo-wen Xing
Chemical Communications 2016 vol. 52(Issue 67) pp:10233-10236
Publication Date(Web):19 Jul 2016
DOI:10.1039/C6CC05116B
A dialdehyde–diboronate-functionalized tetraphenylethene (TPE-DABF) was reported as a H2O2-specific AIE luminogen. TPE-DABF, bearing multiple reductive units (aldehyde, boronate and fructose) in one molecule, afforded an excellent H2O2 selectivity over other ROS in biological buffer, and can be used for sensitive detection of glucose under neutral conditions.
Co-reporter:Yuan Zhang, Rong-fang Ma, Hai-juan Lv, Hong-mei Fang, Chen-yu Xue, Gui-jun Zhang, Xue-ying Wang, Guo-wen Xing
Tetrahedron Letters 2016 Volume 57(Issue 41) pp:4624-4628
Publication Date(Web):12 October 2016
DOI:10.1016/j.tetlet.2016.09.013
•3-AminoBODIPYs were synthesized by the coupling of amines with 2-BODIPY-borates.•5a was a colorimetric and ratiometric fluorescent pH probe at alkaline pH range.•5a was used to discriminate basic amino acids from neutral and acidic amino acids.3-AminoBODIPY derivatives (5a–e) were unexpectedly synthesized by the coupling of amines with 2-BODIPY-borates in the presence of copper(II) acetate Cu(OAc)2 and tetramethylethylenediamine (TMEDA) in the air at room temperature. 5a (pKa = 9.18) was found to be a novel colorimetric and ratiometric fluorescent pH probe at alkaline pH ranges.
Co-reporter:Hai-juan Lv, Rong-fang Ma, Xiao-tai Zhang, Mei-han Li, Yu-tong Wang, Shu Wang, Guo-wen Xing
Tetrahedron 2016 Volume 72(Issue 35) pp:5495-5501
Publication Date(Web):1 September 2016
DOI:10.1016/j.tet.2016.07.039
Recent investigations revealed the close relationship between H2S and HNO in biological systems. It is significant to develop an efficient fluorescent sensor to realize the discriminative sensing of HNO and H2S. Herein, we designed and synthesized a novel fluorescent sensor (CuHCD) with hemicyanine-carbazole as fluorophore and bipyridine-triazole-Cu2+complex as receptor, which enabled the selective recognition of HNO and H2S, respectively via the non-covalent modulation of surfactant assemblies. The CuHCD/surfactant sensor system exhibited excellent selectivity for H2S at 5 mM SDS in HEPES buffer, and displayed high specificity for HNO at 1 mM SDS in HEPES buffer over other common anions and reactive species. Different detection mechanisms in sensing H2S and HNO were deeply investigated. The results showed that H2S seized Cu2+ from the complex to recover the fluorescence of HCD, while HNO reduced Cu2+ to Cu+ in the complex to turn on the fluorescence. In different SDS micellar systems, HCD possessed different dispersity and binding capacity with Cu2+, which led to the selective detection of H2S and HNO, respectively. The hypothesis was further confirmed by replacing SDS micelles with liposome under the same conditions.A CuHCD/surfactant sensor system was constructed to exhibit excellent selectivity for H2S at higher SDS concentrations, and display high specificity for HNO at lower SDS concentrations.
Co-reporter:Guang-jian Liu, Xiao-tai Zhang and Guo-wen Xing
Chemical Communications 2015 vol. 51(Issue 64) pp:12803-12806
Publication Date(Web):02 Jul 2015
DOI:10.1039/C5CC03617H
Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.
Co-reporter:Xiao-tai Zhang, Zhen-yuan Gu, Libing Liu, Shu Wang and Guo-wen Xing
Chemical Communications 2015 vol. 51(Issue 41) pp:8606-8609
Publication Date(Web):10 Apr 2015
DOI:10.1039/C5CC01907A
A sugar epitope, α-(2,9)-trisialic acid, was synthesized and labeled by cyanine dyes through Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC). The cyanine tagged oligosialic acid can be utilized as an efficient fluorescent probe to image the glycan-binding receptors on PC-12 cells. The distribution of Sia-binding immunoglobulin-like lectins (Siglecs) for α-(2,9)-trisialic acid was visualized by Cy3/Cy5 or FRET channel fluorescence imaging.
Co-reporter:Xiao-tai Zhang; Shu Wang; Guo-wen Xing
Chemistry – An Asian Journal 2015 Volume 10( Issue 12) pp:2594-2598
Publication Date(Web):
DOI:10.1002/asia.201500743
Abstract
N,N-Di-2-picolylamine (DPA)-derived diboronic acid receptors (NHBAs) with a flexible linker were designed and synthesized in this study, and two-component sensing ensembles based on cationic NHBAs and an anionic fluorescent indicator 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (HPTS) were successfully developed for both monosaccharides and disaccharides sensing. The dibranched ortho-substituted receptor NHoBA exhibited unexpected selectivity towards lactose among five disaccharides used. The discrimination of five disaccharides and six monosaccharides was finally achieved by the integrated sensor array through linear discriminant analysis (LDA).
Co-reporter:Qin-chao Xu, Hai-juan Lv, Zi-qi Lv, Min Liu, Yang-jie Li, Xiang-feng Wang, Yuan Zhang and Guo-wen Xing
RSC Advances 2014 vol. 4(Issue 88) pp:47788-47792
Publication Date(Web):22 Sep 2014
DOI:10.1039/C4RA07923J
A tailor-made ratiometric fluorescent probe for nucleoside polyphosphates was fabricated based on a pyrene-functionalized zinc(II)–BPEA complex. The significant difference in both the fluorescence and 1H NMR signals of the probe on addition of ATP, ADP and AMP enables efficient discrimination between ATP, ADP and AMP.
Co-reporter:Qin-Chao Xu, Xue-Hui Zhu, Can Jin, Guo-Wen Xing and Yuan Zhang
RSC Advances 2014 vol. 4(Issue 7) pp:3591-3596
Publication Date(Web):02 Dec 2013
DOI:10.1039/C3RA45717F
Two new 2-aminobenzamide structural isomers, 4-isoACOBA and 5-isoACOBA, as fluorescent probes for Cd2+ and Zn2+ were fabricated with carbazolone as fluorophore and N,N-bis(2-pyridylmethyl)ethylenediamine (BPEA) as chelator. With Cd2+/Zn2+ as input, the two probes are characteristic of the transformation from “off–on” to “on–off” molecular switch by interchanging the substitution position of the fluorophore from C-4 to C-5 at the benzene ring. 4-IsoACOBA is a Cd2+-specific turn-on fluorescent probe exhibiting good discrimination between Cd2+ and Zn2+ with FCd2+/FZn2+ = 2.48, while 5-isoACOBA is a Zn2+-specific turn-off probe with FCd2+/FZn2+ = 4.50. The binding behaviours of 4-isoACOBA–Cd(II) and 5-isoACOBA–Zn(II) were deeply investigated by UV and fluorescence titration, ESI-MS analysis, and DFT study. The results indicate that both the electron donating/withdrawing ability and the substituted position of the fluorophore have remarkable influences on the probe sensing properties and selectivity.
Co-reporter:Xiao-tai Zhang, Zhen-yuan Gu, Guo-wen Xing
Carbohydrate Research 2014 Volume 388() pp:1-7
Publication Date(Web):31 March 2014
DOI:10.1016/j.carres.2014.02.006
•The sialylations of four p-toluenethiosialoside donors were thoroughly studied.•The acceptor amount and the promoter have great influence on the sialylation.•The configuration of N-acetylated sialyl donors has little effect on the coupling.•The N-deacetylated α/β sialyl donors show complex sialylation profiles.Four types of 5-N,4-O-carbonyl-protected p-toluenethiosialosides were synthesized and their couplings with different acceptors were thoroughly investigated. The results indicate that the sialyl donor structure, the amount of glycosyl acceptor, and the detailed promotion conditions have great influence on the sialylation stereoselectivties and product yields. Under the (p-Tol)2SO/Tf2O activation conditions, the glycosylations with simple alcohols provided declined α-selectivities and higher yields with increasing the amounts of acceptors from 1.1 equiv to 2.0 equiv. However, the outcome of same sialylation was independent of the relative amounts of sugar alcohol acceptors. With NIS/TfOH as promoter, the α-selectivities of the sialylations were significantly improved compared with the cases activated by (p-Tol)2SO/Tf2O. In general, the difference in configuration of N-acetylated sialyl donors (D2 and D4) has little effect on the sialylation yield and stereoselectivity. In contrast, the N-deacetylated α/β sialyl donors (D1 and D3) show complex sialylation profiles with different acceptors.
Co-reporter:Zhen-yuan Gu, Xiao-tai Zhang, Jia-xin Zhang and Guo-wen Xing
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 30) pp:5017-5022
Publication Date(Web):10 Jun 2013
DOI:10.1039/C3OB40876K
Based on a preactivation protocol with (p-Tol)2SO/Tf2O, a practical, straightforward, and high-yielding synthesis of α-sialyl C-glycosides was accomplished by coupling N-acetyl-5-N,4-O-oxazolidione protected thiosialoside with various trimethylsilyl enol ethers and allyltrimethylsilanes. High yields and excellent α-selectivities were obtained for the strong π-nucleophiles with large nucleophilicity values (N = 4.4–9.0), irrespective of whether silyl enol ethers, silyl ketene acetals or allyltrimethylsilanes were used for the electrophilic C-sialylation.
Co-reporter:Qin-chao Xu, Xiang-feng Wang, Guo-wen Xing and Yuan Zhang
RSC Advances 2013 vol. 3(Issue 36) pp:15834-15841
Publication Date(Web):02 Jul 2013
DOI:10.1039/C3RA41897A
A new mononuclear Zn(II) complex based receptor for PPi sensing and alkaline phosphatase assay was fabricated using 2-aminobenzamide as a scaffold, appended with N,N-bis(2-pyridylmethyl) ethylenediamine (BPEA) and amide as a chelator and carbazole as a fluorophore. Based on an “ON–OFF–ON” molecular switch with zinc ion and PPi inputs, two highly efficient fluorescent chemosensors (4- and 5-isoACBA) were developed, which show a large binding affinity (Ka ≈ 2.5 × 1010 M−2) and high selectivity for PPi (43–48 fold fluorescent enhancement) over a wide range of anions including Pi, AMP, ADP and ATP in an aqueous HEPES buffer (pH 7.4). The binding mode of isoACBA–Zn(II) in the absence or presence of PPi was thoroughly investigated by UV and fluorescence titrations, ESI-HRMS analysis, and DFT studies. The results reveal that the synergistic effects of metal coordination and hydrogen bonding interactions in the structures of the isoACBAs should contribute to the remarkable binding affinity and high sensing selectivity for PPi.
Co-reporter:Jia Jia, Qin-Chao Xu, Ri-chen Li, Xi Tang, Ying-Fang He, Meng-Yu Zhang, Yuan Zhang and Guo-Wen Xing
Organic & Biomolecular Chemistry 2012 vol. 10(Issue 31) pp:6279-6286
Publication Date(Web):21 Jun 2012
DOI:10.1039/C2OB25852H
Three fluorescent probes CdABA′, CdABA and ZnABA′, which are structural isomers of ZnABA, have been designed with N,N-bis(2-pyridylmethyl) ethylenediamine (BPEA) as chelator and 2-aminobenzamide as fluorophore. These probes can be divided into two groups: CdABA, CdABA′ for Cd2+ and ZnABA, ZnABA′ for Zn2+. Although there is little difference in their chemical structures, the two groups of probes exhibit totally different fluorescence properties for preference of Zn2+ or Cd2+. In the group of Zn2+ probes, ZnABA/ZnABA′ distinguish Zn2+ from Cd2+ with FZn2+–FCd2+ = 1.87–2.00. Upon interchanging the BPEA and carbamoyl groups on the aromatic ring of the fluorophore, the structures of ZnABA/ZnABA′ are converted into CdABA/CdABA′. Interestingly, the metal ions selectivity of CdABA/CdABA′ was switched to discriminate Cd2+ from Zn2+ with FCd2+–FZn2+ = 2.27–2.36, indicating that a small structural modification could lead to a remarkable change of the metal ion selectivity. 1H NMR titration and ESI mass experiments demonstrated that these fluorescent probers exhibited different coordination modes for Zn2+ and Cd2+. With CdABA′ as an example, generally, upon addition of Cd2+, the fluorescence response possesses PET pathway to display no obvious shift of maximum λem in the absence or presence of Cd2+. However, an ICT pathway could be employed after adding Zn2+ into the CdABA′ solution, resulting in a distinct red-shift of maximal λem.
Co-reporter:Zhen-yuan Gu;Dr. Jia-xin Zhang ;Dr. Guo-wen Xing
Chemistry – An Asian Journal 2012 Volume 7( Issue 7) pp:1524-1528
Publication Date(Web):
DOI:10.1002/asia.201200172
Co-reporter:Ya-juan Wang;Zhen-yuan Gu ;Dr. Guo-wen Xing
Chemistry – An Asian Journal 2012 Volume 7( Issue 3) pp:489-492
Publication Date(Web):
DOI:10.1002/asia.201100778
Co-reporter:Jia Jia;Zhen-yuan Gu;Ri-chen Li;Ming-hao Huang;Cai-shuang Xu;Yi-fei Wang;Yun-sheng Huang
European Journal of Organic Chemistry 2011 Volume 2011( Issue 24) pp:4609-4615
Publication Date(Web):
DOI:10.1002/ejoc.201100388
Abstract
Four novel Zn2+ fluorescent sensors have been designed with N,N-bis(2-pyridylmethyl)ethylenediamine as chelator and 2-aminobenzamide as fluorophore. These sensors were prepared in two or three steps from readily available starting materials. Of the four designed sensors, ZnABA was found to be the most efficient Zn2+-specific fluorescent probe and has good solubility in biological buffer, a large Stokes shift (186 nm), a high off–on fluorescence response (16-fold enhancement), and distinct selectivity towards Zn2+ over other metal ions. Our results have demonstrated an excellent linear relationship between the fluorescence intensity of ZnABA and the Zn2+ concentration from 0 to 10 μM, which indicates that ZnABA has the potential to be used for the quantitative determination of Zn2+ in an aqueous environment.
Co-reporter:Ya-Juan Wang, Jia Jia, Zhen-Yuan Gu, Fen-Fen Liang, Ri-Chen Li, Ming-Hao Huang, Cai-Shuang Xu, Jia-Xin Zhang, Yi Men, Guo-Wen Xing
Carbohydrate Research 2011 Volume 346(Issue 11) pp:1271-1276
Publication Date(Web):16 August 2011
DOI:10.1016/j.carres.2011.04.029
An N-acetyl-5-N,4-O-oxazolidinone-protected p-toluene 2-thio-sialoside donor, promoted by Ph2SO/Tf2O/TTBPy, was thoroughly investigated in the coupling to various acceptors. The stereoselectivity of the sialylation was found to be dependent on the various reaction conditions, such as pre-activation time, reaction time, the amount of Ph2SO, and TTBPy. A detailed Ph2SO/Tf2O-promoted glycosylation mechanism was proposed, which contained three crucial reactive species: an oxacarbenium ion, C2-sialyloxosulfonium salts, and oxosulfonium supramers. Our research results indicate that it is possible to tune the stereoselectivity of the sialylation by carefully changing the reaction conditions. For instance, Ph2SO (2.0–3.0 equiv)/TTBPy (0–1.0 equiv) promotion gives higher α-selective sialylation in dichloromethane, while Ph2SO (4–5 equiv)/TTBPy (0 equiv) or Ph2SO (2.0 equiv)/TTBPy (2.0 equiv) affords lower stereoselectivity.
Co-reporter:Huai-Qiang Ju, Yang-Fei Xiang, Bao-Juan Xin, Ying Pei, Jia-Xin Lu, Qiao-Li Wang, Min Xia, Chui-Wen Qian, Zhe Ren, Sha-Yan Wang, Yi-Fei Wang, Guo-Wen Xing
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 6) pp:1675-1677
Publication Date(Web):15 March 2011
DOI:10.1016/j.bmcl.2011.01.098
In this study, a novel Hsp90 inhibitor BJ-B11, was synthesized and evaluated for in vitro antiviral activity against several viruses. Possible anti-HSV-1 mechanisms were also investigated. BJ-B11 displayed no antiviral activity against coxsackievirus B3 (CVB3), human respiratory syncytial virus (RSV) and influenza virus (H1N1), but exhibited potent anti-HSV-1 and HSV-2 activity with EC50 values of 0.42 ± 0.18 μM and 0.60 ± 0.21 μM, respectively. Additionally, the inhibitory effects of BJ-B11 against HSV-1 were likely to be introduced at early stage of infection. Our results indicate that BJ-B11 with alternative mechanisms of action is potent as an anti-HSV clinical trial candidate.
Co-reporter:Ya-juan Wang;Bao-juan Xin;Xin-rui Duan;Shu Wang
Macromolecular Rapid Communications 2010 Volume 31( Issue 16) pp:1473-1478
Publication Date(Web):
DOI:10.1002/marc.201000165
Co-reporter:Bao-juan Xin;Shu-feng Si Dr. Dr.
Chemistry – An Asian Journal 2010 Volume 5( Issue 6) pp:1389-1394
Publication Date(Web):
DOI:10.1002/asia.200900696
Abstract
The use of nanobiocatalysts, with the combination of nanotechnology and biotechnology, is considered as an exciting and rapidly emerging area. The use of iron oxide magnetic nanoparticles, as enzyme immobilization carriers, has drawn great attention because of their unique properties, such as controllable particle size, large surface area, modifiable surface, and easy recovery. In this study, various γ-Fe2O3/Fe3O4 magnetic nanoparticles with immobilized proteases were successfully prepared by three different immobilization strategies including A) direct binding, B) with thiophene as a linker, and C) with triazole as a linker. The oligopeptides syntheses catalyzed by these magnetic nanoparticles (MNPs) with immobilized proteases were systematically studied. Our results show that i) for magnetic nanoparticles immobilized α-chymotrypsin, both immobilization strategies A and B furnished good reusability for the Z-Tyr-Gly-Gly-OEt synthesis, the MNPs enzymes can be readily used at least five times without significant loss of its catalytic performance: ii) In the case of Z-Asp-Phe-OMe synthesis catalyzed by magnetic nanoparticles immobilized thermolysin, immobilization Strategy B provided the best recyclability: iii) For the immobilized papain, although Strategy A or B afforded an immobilized enzyme for the first cycle of Z-Ala-Leu-NHNHPh synthesis in good yield, their subsequent catalytic activity decreased rapidly. In general, the γ-Fe2O3 MNPs were better for use as an immobilization matrix, rather than the Fe3O4 MNPs, owing to their smaller particle size and higher surface area.
Co-reporter:Guo-wen Xing;Li Chen ;Fen-fen Liang
European Journal of Organic Chemistry 2009 Volume 2009( Issue 34) pp:5963-5970
Publication Date(Web):
DOI:10.1002/ejoc.200900778
Abstract
Ganglioside GM3 [α-Neu5Ac-(2,3)-β-Gal-(1,4)-β-Glc-(1,1)-Cer; 1] is considered as an important tumor-associated carbohydrate antigen, which can be used in the development of tumor vaccine. In this study, a facile and convergent synthetic strategy for GM3 was developed, and the preparation of three building blocks started from the most readily available compounds sialic acid, lactose, and L-serine. Ceramide aglycon 9 was constructed from L-serine in 13 steps with 6 % overall yield, and lactosyl trichloroacetimidate 14 was synthesized from lactose in 7 steps with 25 % yield. With novel N-acetyl-5-N,4-O-oxazolidinone protected p-toluenethiosialoside 15 as donor, which was developed by our group, the sialylation of benzoyl-protected lactosyl ceramide diol 23 was successfully accomplished in 54 % yield. Our strategy here provides a shorter linear total synthesis of GM3 in five steps and with 26 % overall yield. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Co-reporter:Zhen-yuan Gu, Xiao-tai Zhang, Jia-xin Zhang and Guo-wen Xing
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 30) pp:NaN5022-5022
Publication Date(Web):2013/06/10
DOI:10.1039/C3OB40876K
Based on a preactivation protocol with (p-Tol)2SO/Tf2O, a practical, straightforward, and high-yielding synthesis of α-sialyl C-glycosides was accomplished by coupling N-acetyl-5-N,4-O-oxazolidione protected thiosialoside with various trimethylsilyl enol ethers and allyltrimethylsilanes. High yields and excellent α-selectivities were obtained for the strong π-nucleophiles with large nucleophilicity values (N = 4.4–9.0), irrespective of whether silyl enol ethers, silyl ketene acetals or allyltrimethylsilanes were used for the electrophilic C-sialylation.
Co-reporter:Xiao-tai Zhang, Zhen-yuan Gu, Libing Liu, Shu Wang and Guo-wen Xing
Chemical Communications 2015 - vol. 51(Issue 41) pp:NaN8609-8609
Publication Date(Web):2015/04/10
DOI:10.1039/C5CC01907A
A sugar epitope, α-(2,9)-trisialic acid, was synthesized and labeled by cyanine dyes through Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC). The cyanine tagged oligosialic acid can be utilized as an efficient fluorescent probe to image the glycan-binding receptors on PC-12 cells. The distribution of Sia-binding immunoglobulin-like lectins (Siglecs) for α-(2,9)-trisialic acid was visualized by Cy3/Cy5 or FRET channel fluorescence imaging.
Co-reporter:Guang-jian Liu, Xiao-tai Zhang and Guo-wen Xing
Chemical Communications 2015 - vol. 51(Issue 64) pp:NaN12806-12806
Publication Date(Web):2015/07/02
DOI:10.1039/C5CC03617H
Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.
Co-reporter:Guang-Jian Liu, Zi Long, Hai-juan Lv, Cui-yun Li and Guo-wen Xing
Chemical Communications 2016 - vol. 52(Issue 67) pp:NaN10236-10236
Publication Date(Web):2016/07/19
DOI:10.1039/C6CC05116B
A dialdehyde–diboronate-functionalized tetraphenylethene (TPE-DABF) was reported as a H2O2-specific AIE luminogen. TPE-DABF, bearing multiple reductive units (aldehyde, boronate and fructose) in one molecule, afforded an excellent H2O2 selectivity over other ROS in biological buffer, and can be used for sensitive detection of glucose under neutral conditions.
Co-reporter:Jia Jia, Qin-Chao Xu, Ri-chen Li, Xi Tang, Ying-Fang He, Meng-Yu Zhang, Yuan Zhang and Guo-Wen Xing
Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 31) pp:NaN6286-6286
Publication Date(Web):2012/06/21
DOI:10.1039/C2OB25852H
Three fluorescent probes CdABA′, CdABA and ZnABA′, which are structural isomers of ZnABA, have been designed with N,N-bis(2-pyridylmethyl) ethylenediamine (BPEA) as chelator and 2-aminobenzamide as fluorophore. These probes can be divided into two groups: CdABA, CdABA′ for Cd2+ and ZnABA, ZnABA′ for Zn2+. Although there is little difference in their chemical structures, the two groups of probes exhibit totally different fluorescence properties for preference of Zn2+ or Cd2+. In the group of Zn2+ probes, ZnABA/ZnABA′ distinguish Zn2+ from Cd2+ with FZn2+–FCd2+ = 1.87–2.00. Upon interchanging the BPEA and carbamoyl groups on the aromatic ring of the fluorophore, the structures of ZnABA/ZnABA′ are converted into CdABA/CdABA′. Interestingly, the metal ions selectivity of CdABA/CdABA′ was switched to discriminate Cd2+ from Zn2+ with FCd2+–FZn2+ = 2.27–2.36, indicating that a small structural modification could lead to a remarkable change of the metal ion selectivity. 1H NMR titration and ESI mass experiments demonstrated that these fluorescent probers exhibited different coordination modes for Zn2+ and Cd2+. With CdABA′ as an example, generally, upon addition of Cd2+, the fluorescence response possesses PET pathway to display no obvious shift of maximum λem in the absence or presence of Cd2+. However, an ICT pathway could be employed after adding Zn2+ into the CdABA′ solution, resulting in a distinct red-shift of maximal λem.