Michael C. Pirrung

Find an error

Name: Pirrung, Michael

Organization: University of California , USA

Department: Department of Chemistry

Title: Professor(PhD)

TOPICS

Organic Chemistry

Organic Photochemistry

Chemicals
References

Synthesis and bioluminescence of difluoroluciferin

Co-reporter:Michael C. Pirrung, Goutam Biswas, Natalie De Howitt, Jiayu Liao

Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 20) pp:4881-4883

Publication Date(Web):15 October 2014

DOI:10.1016/j.bmcl.2014.08.048

A new synthesis route to firefly luciferin analogs was developed via the synthesis of 5′,7′-difluoroluciferin. As a luciferase substrate, it produces maximal bioluminescence at a much lower pH than is optimal for native luciferin, and at lower pH it gives much more of the red-shifted emission that is characteristic of the phenolate. These features are attributed to the enhanced acidity of the o,o-difluorophenol.

The genesis of microarrays

Co-reporter:Michael C. Pirrung;Edwin M. Southern

Biochemistry and Molecular Biology Education 2014 Volume 42( Issue 2) pp:106-113

Publication Date(Web):

DOI:10.1002/bmb.20756

Abstract

This review provides a perspective on the initial development of microarray technologies by two independent groups in the late 1980s. © 2013 by The International Union of Biochemistry and Molecular Biology, 42(2):106–113, 2014.

Catalyzed Claisen rearrangements of O-allyl kojates

Co-reporter:Michael C. Pirrung, Jenifer N. Nalbandian

Tetrahedron Letters 2013 Volume 54(Issue 29) pp:3752-3754

Publication Date(Web):17 July 2013

DOI:10.1016/j.tetlet.2013.05.002

Allylic ethers of kojic acid undergo Claisen rearrangement with catalysis by zinc triflate to give the corresponding C-allylated kojic acids in moderate to good yields.

Reactive Esters in Amide Ligation with -Hydroxyamines

Co-reporter:Michael C. Pirrung;Fa Zhang;Sudhakar Ambadi;Tannya R. Ibarra-Rivera

European Journal of Organic Chemistry 2012 Volume 2012( Issue 23) pp:4283-4286

Publication Date(Web):

DOI:10.1002/ejoc.201200624

Abstract

Amide formation between mildly activated esters and 1,2-amino alcohols occurs without the need for coupling reagents. The reaction pathway involves facile intermolecular transesterification and intramolecular ON transacylation. The method is environmentally friendly and offers no risk of racemization via highly activated acylating intermediates.

Syntheses and cytotoxicity of syringolin B-based proteasome inhibitors

Co-reporter:Tannya R. Ibarra-Rivera, John Opoku-Ansah, Sudhakar Ambadi, André S. Bachmann, Michael C. Pirrung

Tetrahedron 2011 67(51) pp: 9950-9956

Publication Date(Web):

DOI:10.1016/j.tet.2011.09.048

Total Synthesis of Syringolin A and B

Co-reporter:Michael C. Pirrung, Goutam Biswas and Tannya R. Ibarra-Rivera

Organic Letters 2010 Volume 12(Issue 10) pp:2402-2405

Publication Date(Web):April 28, 2010

DOI:10.1021/ol100761z

Total syntheses of two recently discovered proteasome inhibitors, syringolin A and B, are reported. The key to our approach was creation of the α,β-unsaturated 12-membered lactam via intramolecular Horner−Wadsworth−Emmons reaction. Such reactions have been broadly used to prepared macrolactones, but this work presents a rarer example of its application to macrolactams. The final steps involved attachment of the bis(valinyl)urea side chain using peptide coupling procedures, including a method based on the unprotected valine N-carboxy anhydride. The additional alkene of syringolin A was created through cross-metathesis.

Iodine scanning of a phenazine inhibitor of vacuolar sorting

Co-reporter:Marci Surpin, Yunfan Zou, Chiyi Xiong, Natasha V. Raikhel, Michael C. Pirrung

Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 5) pp:1496-1499

Publication Date(Web):1 March 2010

DOI:10.1016/j.bmcl.2010.01.106

Affinity reagents are often used to address the target identification problem in chemical genetics. The design of such reagents so that the linker does not occlude interactions with protein targets is an ongoing challenge. This work describes a systematic approach to synthesize derivatives of a bioactive that should avoid interference with binding to targets and be readily converted to affinity reagents.The synthesis and biological activity of N-phenylphenazin-2-amine and 4 iodinated derivatives is reported.

Structure-reactivity relationships in (2-hydroxyethyl)benzophenone photoremovable protecting Groups

Co-reporter:Michael C. Pirrung, Biswajit Gopal Roy, Surendra Gadamsetty

Tetrahedron 2010 66(17) pp: 3147-3151

Publication Date(Web):

DOI:10.1016/j.tet.2010.02.087

His-tags lighten up and lose their inhibitions

Co-reporter:Michael C. Pirrung;

Proceedings of the National Academy of Sciences 2010 107(14) pp:6123-6124

Publication Date(Web):April 2, 2010

DOI:10.1073/pnas.1002011107

Multicomponent Reactions of Cyclobutanones

Co-reporter:Michael C. Pirrung and Jianmei Wang

The Journal of Organic Chemistry 2009 Volume 74(Issue 8) pp:2958-2963

Publication Date(Web):March 18, 2009

DOI:10.1021/jo802170k

Cyclobutanones are essentially unknown as reactants in isonitrile-based multicomponent reactions. Ugi reactions of cyclobutanone and Passerini reactions of tetramethylcyclobutane-1,3-dione have been performed in this work. These reactions are significantly enhanced by being conducted in water, a subject of recent interest whose basis is still in question but whose effects are beyond doubt. The Ugi reaction of cyclobutanone has been used in a brief synthesis of an aspartame analogue.

Multicomponent Reactions of Convertible Isonitriles

Co-reporter:Michael C. Pirrung, Subir Ghorai and Tannya R. Ibarra-Rivera

The Journal of Organic Chemistry 2009 Volume 74(Issue 11) pp:4110-4117

Publication Date(Web):May 1, 2009

DOI:10.1021/jo900414n

A new family of unsaturated isonitriles has been prepared by the base-promoted ring-opening of oxazoles, offering an alternative to the conventional formamide dehydration route. These compounds undergo the full complement of multicomponent reactions for which isonitriles are known and offer the desirable trait of giving amide products that readily participate in acyl substitution reactions (hence, they are convertible). Moreover, they do not have the objectionable odors for which isonitriles are typically known, making them more accessible as reagents for organic synthesis. One focus of the work is isonitriles bearing perfluorinated alkyl groups that enable the ready separation of such reagents from nonfluorinated reaction products using the “light” fluorous method of fluorous solid-phase extraction.

Ethylene Receptor Antagonists: Strained Alkenes Are Necessary but Not Sufficient

Co-reporter:Michael C. Pirrung, Anthony B. Bleecker, Yoshihisa Inoue, Fernando I. Rodríguez, Norimitsu Sugawara, Takehiko Wada, Yunfan Zou, Brad M. Binder

Chemistry & Biology 2008 Volume 15(Issue 4) pp:313-321

Publication Date(Web):21 April 2008

DOI:10.1016/j.chembiol.2008.02.018

Plants use ethylene as a hormone to control many physiological processes. Ethylene perception involves its binding to an unusual copper-containing, membrane-bound receptor. Inhibitors of ethylene action are valuable to study signaling and may have practical use in horticulture. Past investigation of alkene ligands for this receptor has identified strain as the key factor in antagonism of ethylene binding and action, consistent with known trends in metal-alkene complex stability. However, in this work, this principle could not be extended to other alkenes, prompting development of the proposal that a ring-opening reaction accounts for the unusual potency of cyclopropene ethylene antagonists. Another factor augmenting the affinity of alkenes for the copper binding site is pyramidalization, as in trans-cycloalkenes. The enantiomeric selectivity in the binding of one such alkene to the ethylene receptor demonstrates its protein-composed asymmetric environment.

Quinone Replacements for Small Molecule Insulin Mimics

Co-reporter:Michael C. Pirrung Dr.;Liu Deng Dr.;Bo Lin Dr.;Nicholas J. G. Webster Dr.

ChemBioChem 2008 Volume 9( Issue 3) pp:360-362

Publication Date(Web):

DOI:10.1002/cbic.200700597

Mechanistic Studies on the Photochemical Deprotection of 3′,5′-Dimethoxybenzoin Esters

Co-reporter:Zheng Zhou;Tong Ye;John D. Simon

Photochemistry and Photobiology 2006 Volume 82(Issue 5) pp:1258-1264

Publication Date(Web):30 APR 2007

DOI:10.1562/2006-02-07-RA-798

Several mechanistic alternatives proposed for the photochemical deprotection of dimethoxybenzoin esters are presented. Both experimental and theoretical evidence suggest the mechanism is heterolysis of the singlet excited state to form a carbox-ylate and the α-ketocation. The α-ketocation has been observed by transient spectroscopy. We propose the α-ketocation undergoes electrocyclization to an intermediate with extended conjugation, whose deprotonation gives the observed benzofuran product. A Brønsted study of the rates of benzofuran formation with dimethoxybenzoin esters derived from acids of varying pK_a shows the rate is independent of the basicity of the leaving group. In this multistep reaction, benzofuran formation by a final deprotonation is slower than α-ketocation generation.

Acceleration of Organic Reactions through Aqueous Solvent Effects

Co-reporter:Michael C. Pirrung Dr.

Chemistry - A European Journal 2006 Volume 12(Issue 5) pp:

Publication Date(Web):28 SEP 2005

DOI:10.1002/chem.200500959

The parallels between organic reactions conducted with water as the solvent and reactions conducted under high pressure can be understood in light of theories of aqueous solvation and hydrophobic effects. Such parallels provide powerful tools for promoting reactions of nonpolar compounds.