Modifications of amino acids using arenediazonium salts

Aryl transfer reactions from arenediazonium salts have started to make their impact in chemical biology with initial forays in the arena of arylative modifications and bio-conjugations of amino acids, peptides and proteins. The unique multimodal reactivity of arenediazonium salts, ranging from therm...

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Published inOrganic & biomolecular chemistry Vol. 17; no. 36; pp. 838 - 8329
Main Authors Sengupta, Saumitra, Chandrasekaran, Srinivasan
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 28.09.2019
Subjects
Amino acids
Amino Acids - chemistry
Aromatic compounds
Chemical reactions
Conjugation
Coupling
Diazonium Compounds - chemistry
Hydrocarbons, Aromatic - chemistry
Immobilization
Labeling
Molecular Conformation
Organic chemistry
Peptides
Photochemical reactions
Photochemicals
Proteins
Salts
Salts - chemistry
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Summary:Aryl transfer reactions from arenediazonium salts have started to make their impact in chemical biology with initial forays in the arena of arylative modifications and bio-conjugations of amino acids, peptides and proteins. The unique multimodal reactivity of arenediazonium salts, ranging from thermal or photochemical radical chain reactions, Pd-catalyzed coupling to arylazo-coupling reactions, all under distinct but mild conditions, provides multiple options for side chain modifications of amino acids and peptides and in addition, site-selective protein conjugation and labelling, protein immobilization, azo-bridged macrocyclization, etc . under bio-ambient conditions. The purpose of this review is to highlight these recent advances and to stimulate interest towards broader applications of arenediazonium salts as aryl transfer agents in bioconjugation reactions. Aryl transfer reactions from arenediazonium salts have started to make their impact in chemical biology with initial forays in the arena of arylative modifications and bio-conjugations of amino acids, peptides and proteins.
Bibliography:Tetrahedron
Chemistry-An Asian Journal
Tetrahedron Letters
and
His research interests include exploitation of new methods and reagents in organic synthesis and their utilization in the synthesis of biologically active natural products.
Saumitra Sengupta, born in Kolkata, India (1957), was trained at the University of Florida (PhD 1987 A R Katritzky), the University of California-Santa Barbara (post-doc 1987-1989 B H Lipshutz) and the University of Waterloo (post-doc 1989-1991 V Snieckus). He joined the chemistry faculty at Jadavpur University in 1991 where his research spanned across Pd-catalyzed reactions of arenediazonium salts, asymmetric synthesis and functional dendrimers. He is a recipient of the CRSI Bronze Medal in 2002. He joined Aurigene Discovery Technologies in 2005 as Vice President, Medicinal Chemistry where he led several drug discovery programs in oncology and inflammation and is credited with the development of three clinical candidates. He moved to TCG Life Sciences in 2011 as Distinguished Scientist and was involved in antibacterial drug discovery until his retirement in 2015. Currently, he is a chemistry consultant and pursues his interests in synthetic methodologies, chemo-sensors and chemical biology through collaborations.
Srinivasan Chandrasekaran was born in Tamil Nadu, India in 1945. He received his early education at the University of Madras and obtained his PhD degree in 1972 working with Prof. S. Swaminathan at the University of Madras. He worked as a Research Associate (1973-75, 1976-77) with Prof. E. J. Corey at Harvard University, USA, and also at Syntex Research, USA (1976). He started independent research at the Department of Chemistry, Indian Institute of Technology, Kanpur, where he was promoted as Professor in 1985. In May 1989, he moved to the Indian Institute of Science, Bangalore where he is currently working as INSA Distinguished Professor in the Department of Organic Chemistry. He has received the Shanti Swarup Bhatnagar Prize (Council of Scientific and Industrial Research, 1989). He is an elected fellow of the Indian Academy of Sciences, the Indian National Science Academy, and The World Academy of Sciences (TWAS). He served as a member of the International Advisory Board of
and Regional Editor of
He was an elected member of the Bureau and Executive committee of the International Union of Pure and Applied Chemistry. At present he serves as a member of the International Advisory Board of
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ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01471c