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Oxyma‐based phosphates for racemization‐free peptide segment couplings
Author(s) -
Mitachi Katsuhiko,
Kurosu Yuki E.,
Hazlett Brandon T.,
Kurosu Michio
Publication year - 2016
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.2859
Subject(s) - racemization , reagent , chemistry , peptide , amide , peptide synthesis , oligopeptide , amino acid , combinatorial chemistry , aqueous solution , coupling reaction , organic chemistry , stereochemistry , catalysis , biochemistry
Glyceroacetonide–Oxyma [(2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)methyl 2‐cyano‐2‐(hydroxyimino)acetate ( 1 )] displayed remarkable physico‐chemical properties as an additive for peptide‐forming reactions. Although racemization‐free amide‐forming reactions have been established for N ‐urethane‐protected α ‐amino acids with EDCI, 1 , and NaHCO 3 in water or DMF‐water media, amide‐forming reactions of N ‐acyl‐protected α ‐amino acids and segment couplings of oligopeptides still require further development. Diethylphosphoryl–glyceroacetonide–oxyma (DPGOx 3 ) exhibits relative stability in aprotic solvents and is an effective coupling reagent for N ‐acyl‐protected α ‐amino acids and oligo peptide segments. The conditions reported here is also effective in lactam‐forming reactions. Unlike most of the reported coupling reagents, simple aqueous work‐up procedures can remove the reagents and by‐products generated in the reactions. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.