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Dehydroalanine‐Containing Peptides by AcOH‐Elimination from O ‐Acetylserine Residuces with DBU/LiClO 4 in Tetrahydrofuran
Author(s) -
Sommerfeld Thimo L.,
Seebach Dieter
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760427
Subject(s) - chemistry , dehydroalanine , acylation , serine , tetrahydrofuran , yield (engineering) , stereochemistry , epimer , peptide , amino acid , racemization , organic chemistry , biochemistry , catalysis , materials science , solvent , metallurgy , enzyme
The elimination of H 2 O from serine residues in peptides was found to be feasible by the following two steps: O ‐acylation with AcCl/pyrideine in CH 2 Cl 2 and treatment with an imidine base (DBU or DBN) in THF in the presence of large amounts of LiClO 4 (10 examples). Other Li salts such as LiBr and LiCl can also be used. No epimerization of the amino acid residues in te peptide could be detected under these conditions. Thus, a simple method for the preparation of peptides with dehydroalanine residues in high yield, directly from serine‐containing precursors, is available.