Journal of the American Chemical Society p. 5461 - 5470 (1983)
Update date:2022-08-05
Topics:
Aberhart, D. John
Gould, Steven J.
Lin, Horng-Jau
Thiruvengadam, T. K.
Weiller, Bruce H.
The stereochemistry of lysine 2,3-aminomutase in Clostridium subterminale strain SB4 has been elucidated.Deuterium NMR has been used to show that the transformation of (2S)-α-lysine to (3S)-β-lysine proceeds with transfer of the 3-pro-R hydrogen of α-lysine to the 2-pro-R position of β-lysine.Also the C-2 hydrogen of α-lysine is retained at 2-pro-S position of β-lysine.Thus, the reaction proceeds with inversion of configuration at C-2 and C-3.Experiments with <2-15N,3-13C>-α-lysine have shown that the amino group transfer takes place completely intramolecularly.However, conversion of α-lysine-3,3-d2 led to the formation of mainly β-lysine-d1 indicating substantially or completely intermolecular hydrogen transfer in the reaction.
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