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15 N‐NMR Spectroscopy, 11. Stereospecifity of the Synthesis of Boc‐DL‐Val‐DL‐Val‐OMe
Author(s) -
Kricheldorf Hans R.,
Hull William E.
Publication year - 1978
Publication title -
justus liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0075-4617
DOI - 10.1002/jlac.197819781114
Subject(s) - diastereomer , chemistry , stereochemistry , nuclear magnetic resonance spectroscopy , valine , nmr spectra database , condensation , spectroscopy , spectral line , amino acid , physics , biochemistry , astronomy , quantum mechanics , thermodynamics
36.48 MHz 15 N‐NMR spectra allow one to distinguish the diastereomeric dipeptides Boc‐L‐Val‐L‐Val‐OH and Boc‐L‐Val‐D‐Val‐OH. It is thus possible to control the ratio of L‐L‐ (D‐D‐) and L‐D‐(D‐L‐)dipeptides obtained from the condensation of Boc‐DL‐Val‐OH and DL‐valine methyl ester simply by using natural abundance 15 N‐NMR spectra. The synthesis of Boc‐DL‐Val‐DL‐Val‐OMe was carried out under twelve different experimental conditions.