title: C(alpha)-hydroxymethyl methionine: synthesis, optical resolution and crystal structure of its (+)-N(alpha)-benzoyl derivative.
abstract: (R, S)-Methionine was transformed into C(alpha)-hydroxymethyl methionine by a route involving C(alpha)-hydroxymethylation of 2-phenyl-4-methylthioethyl-5-oxo-4,5-dihydro-1,3-oxazole. The absolute configuration of (-)-C(alpha)-hydroxymethyl methionine was elucidated to be (S) by chemical correlation with (S) (-)-C(alpha)-ethyl serine. Absolute structure determination (by single crystal X-ray diffraction) on N(alpha)-benzoyl-C(alpha)-hydroxymethyl methionine confirmed the (R)-configuration for the (+)-enantiomer. In addition, the X-ray diffraction analysis showed that the C(alpha,alpha)-disubstituted glycyl residue adopts the fully extended (C5) conformation.
authors.affiliation: Institute of Organic Chemistry, Technical University of Lodz, Poland.
authors.forename: R
authors.initials: R
authors.lastname: Witkowska
authors.forename: K
authors.initials: K
authors.lastname: Kaczmarek
authors.forename: M
authors.initials: M
authors.lastname: Crisma
authors.forename: C
authors.initials: C
authors.lastname: Toniolo
authors.forename: J
authors.initials: J
authors.lastname: Zabrocki
mesh_terms: D018360:Crystallography, X-Ray; D008715:Methionine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D010452:Peptide Biosynthesis; D011487:Protein Conformation
chemical_list: C019421:hydroxymethylmethionine; D008715:Methionine