Cα-hydroxymethyl methionine: synthesis, optical resolution and crystal structure of its (+)-Nα-benzoyl derivative

✍ Scribed by Renata Witkowska; Krzysztof Kaczmarek; Marco Crisma; Claudio Toniolo; Janusz Zabrocki

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 113 KB
• Volume: 7
• Category: Article
• ISSN: 1075-2617
• DOI: 10.1002/psc.360

✦ Synopsis

Abstract

(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.