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Linear Stereo‐co‐oligopeptides with Alternating D ‐ and L ‐Residues. I. Synthesis and Mass Spectrometric Behavior of the Members of a Series with Valine Residues
Author(s) -
Tomasic Lera,
Stefani Annibale,
Lorenzi Gian Paolo
Publication year - 1980
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.19800630726
Subject(s) - oligopeptide , chemistry , valine , stereochemistry , condensation , peptide , amino acid , biochemistry , thermodynamics , physics
The synthesis of the protected stereo‐co‐oligopeptides with alternating D ‐ and L ‐valine residues Boc‐( D ‐Val) m ‐( L ‐Val‐ D ‐Val) n ‐OMe (m = 0; n = 1,2,3,4,6,8, and m = 1; n = 1,2,3,4) is described. The synthesis has been carried out by using conventional solution methods. The co‐oligopeptides up to the nonapeptide (m = 1; n = 4) have been prepared in a stepwise fashion. The dodecapeptide (m = 0; n = 6) and the hexadecapeptide (m = 0; n = 8) have been prepared by condensation of smaller peptides, and the criteria used for assessing their stereochemical purity are discussed. Preliminary characterization data are presented. Even the co‐oligopeptides with six or more residues, up to the dodecapeptide included, have given EI/MS. showing the molecular ion peak. The possible reasons for this uncommon behavior are examined.