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Use of Oxyma as pH modulatory agent to be used in the prevention of base‐driven side reactions and its effect on 2‐chlorotrityl chloride resin
Author(s) -
SubirósFunosas Ramon,
ElFaham Ayman,
Albericio Fernando
Publication year - 2011
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.21713
Subject(s) - chemistry , base (topology) , chloride , acid–base reaction , combinatorial chemistry , organic chemistry , medicinal chemistry , mathematics , mathematical analysis
The presence of low pKa N ‐hydroxylamines is beneficial in peptide chemistry as they reduce some base‐mediated side reactions. Here we evaluated the applicability and buffering capacity of Ethyl 2‐cyano‐2‐(hydroxyimino) acetate (Oxyma) in the prevention of aspartimide/piperidide formation and Pro‐based overcoupling and compared it with the performance of HOBt and HOAt. In addition, the compatibility of these additives with the highly acid‐labile 2‐chlorotrityl chloride resin is examined. © 2011 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 98: 89–97, 2012.