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D ‐ or L ‐Alanine: That Is the Question
Author(s) -
Laerdahl Jon K.,
Wesendrup Ralf,
Schwerdtfeger Peter
Publication year - 2000
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/1439-7641(20000804)1:1<60::aid-cphc60>3.0.co;2-m
Subject(s) - homochirality , alanine , enantiomer , conformational isomerism , chemistry , stereochemistry , computational chemistry , molecule , organic chemistry , amino acid , biochemistry
The question is reopened, whether L ‐ or D ‐alanine is more stable. Calculated parity‐violating energy shifts for the 13 stable conformers of gaseous alanine (the picture shows the global minima) indicate that the stabilization of a certain enantiomer is strongly dependent on its conformation. Naturally occurring L ‐alanine is preferred for only seven of the investigated structures, which allows no definite conclusion on the relative stability of the two chiral forms to explain the origin of homochirality in living organisms.