Premium
Synthesis of glyoxylyl peptides using an Fmoc‐protected α,α′‐diaminoacetic acid derivative
Author(s) -
Far Samia,
Melnyk Oleg
Publication year - 2005
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.632
Subject(s) - oxidizing agent , chemistry , glyoxylic acid , peptide , moiety , combinatorial chemistry , derivative (finance) , cleavage (geology) , stereochemistry , protecting group , peptide synthesis , organic chemistry , biochemistry , biology , fracture (geology) , financial economics , economics , paleontology , alkyl
The synthesis of glyoxylyl peptides by coupling the masked glyoxylic acid derivative (FmocNH) 2 CHCO 2 H, 1 , to a peptidyl resin assembled using Fmoc/ tert ‐butyl chemistry has been described recently. Deprotection and cleavage of the peptide from the solid support using TFA was followed by unmasking of the glyoxylyl group in solution in the presence of DBU. [] The glyoxylyl peptide was thus generated using non‐oxidizing conditions by comparison with the method based on the periodic oxidation of a seryl‐precursor. However, base treatment of the (FmocNH) 2 CHCO 2 ‐peptide led to the formation of a byproduct besides the desired glyoxylyl peptide. This paper describes an optimized procedure for unmasking the Fmoc‐protected α,α′‐diaminoacetic acid moiety in solution which suppressed byproduct formation. Also presented is a series of experiments that permitted a structure and a mechanism of formation for the byproduct to be suggested. Copyright © 2005 European Peptide Society and John Wiley & Sons, Ltd.