C(alpha)-hydroxymethyl methionine: synthesis, optical resolution and crystal structure of its (+)-N(alpha)-benzoyl derivative.
(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.
Witkowska
R
R
Institute of Organic Chemistry, Technical University of Lodz, Poland.
Kaczmarek
K
K
Crisma
M
M
Toniolo
C
C
Zabrocki
J
J
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
C019421:hydroxymethylmethionine; D008715:Methionine