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Ethyl 2‐( tert ‐Butoxycarbonyloxyimino)‐2‐cyanoacetate (Boc‐Oxyma) as Coupling Reagent for Racemization‐Free Esterification, Thioesterification, Amidation and Peptide Synthesis
Author(s) -
Thalluri Kishore,
Nadimpally Krishna Chaitanya,
Chakravarty Maharishi Parasar,
Paul Ashim,
Mandal Bhubaneswar
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200645
Subject(s) - chemistry , racemization , peptide synthesis , reagent , hexafluorophosphate , amino acid , peptide , combinatorial chemistry , organic chemistry , ionic liquid , catalysis , biochemistry
Here we report the synthesis and utility of ethyl 2‐( tert ‐butoxycarbonyloxyimino)‐2‐cyanoacetate (Boc‐Oxyma) as an efficient coupling reagent for racemization‐free esterification, thioesterification, amidation reactions and peptide synthesis that uses equimolar amounts of acids and alcohols, thiols, amines or amino acids, respectively. Its application to solid phase as well as solution phase peptide synthesis is also demonstrated and a mechanistic investigation is discussed. Boc‐Oxyma is similar to the well known coupling agent COMU {1‐[1‐cyano‐2‐ethoxy‐2‐oxoethylideneaminooxy)‐dimethylaminomorpholino]uronium hexafluorophosphate} in terms of its high reactivity and mechanism of action. However, it is not only much easier to prepare, but also to recover and reuse, thereby generating far less chemical waste.