By decarboxylation of (2S)-histidine (1) in 2H2O in the presence of histidine decarboxylase from Clostridium welchii, monodeuteriated histamine (2a) was obtained. Ruthenium tetraoxide oxidation of (2a) furnished deuteriated β-alanine (3a), which was converted into the methyl ester of its phthaloyl derivative (6c). This compound showed a negative optical rotation, as did (6a) prepared from (3R)-(3c). From these results an (R)-configuration can be attributed to (2a) and consequently decarboxylation of (1) proceeds with retention of configuration.
On the stereochemistry of the decarboxylation of (2S)-histidine catalysed by histidine decarboxylase from Clostridium welchii (E.C.4.1.1.22) / E. Santaniello, A. Manzocchi, P.A. Biondi. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :0(1981), pp. 307-309.
On the stereochemistry of the decarboxylation of (2S)-histidine catalysed by histidine decarboxylase from Clostridium welchii (E.C.4.1.1.22)
E. SantanielloPrimo
;A. ManzocchiSecondo
;P.A. BiondiUltimo
1981
Abstract
By decarboxylation of (2S)-histidine (1) in 2H2O in the presence of histidine decarboxylase from Clostridium welchii, monodeuteriated histamine (2a) was obtained. Ruthenium tetraoxide oxidation of (2a) furnished deuteriated β-alanine (3a), which was converted into the methyl ester of its phthaloyl derivative (6c). This compound showed a negative optical rotation, as did (6a) prepared from (3R)-(3c). From these results an (R)-configuration can be attributed to (2a) and consequently decarboxylation of (1) proceeds with retention of configuration.
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