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C α ‐hydroxymethyl methionine: synthesis, optical resolution and crystal structure of its (+)‐ N α ‐benzoyl derivative
Author(s) -
Witkowska Renata,
Kaczmarek Krzysztof,
Crisma Marco,
Toniolo Claudio,
Zabrocki Janusz
Publication year - 2001
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.360
Subject(s) - hydroxymethyl , methionine , chemistry , stereochemistry , absolute configuration , crystal structure , enantiomer , residue (chemistry) , crystallography , amino acid , organic chemistry , biochemistry
( R , S )‐Methionine was transformed into C α ‐hydroxymethyl methionine by a route involving C α ‐hydroxymethylation of 2‐phenyl‐4‐methylthioethyl‐5‐oxo‐4,5‐dihydro‐1,3‐oxazole. The absolute configuration of (−)‐ C α ‐hydroxymethyl methionine was elucidated to be ( S ) by chemical correlation with ( S ) (−)‐ C α ‐ethyl serine. Absolute structure determination (by single crystal X‐ray diffraction) on N α ‐benzoyl‐ C α ‐hydroxymethyl methionine confirmed the ( R )‐configuration for the (+)‐enantiomer. In addition, the X‐ray diffraction analysis showed that the C α,α ‐disubstituted glycyl residue adopts the fully extended (C 5 ) conformation. Copyright © 2001 European Peptide Society and John Wiley & Sons, Ltd.