Synthesis of deuterium- and tritium-labeled 6 beta-bromopenicillanic acid

P J Claes; H Vanderhaeghe; E Roets; J Thomis; F De Meester; J L Piette

doi:10.7164/antibiotics.38.75

Synthesis of deuterium- and tritium-labeled 6 beta-bromopenicillanic acid

J Antibiot (Tokyo). 1985 Jan;38(1):75-82. doi: 10.7164/antibiotics.38.75.

Authors

P J Claes, H Vanderhaeghe, E Roets, J Thomis, F De Meester, J L Piette

PMID: 2982779
DOI: 10.7164/antibiotics.38.75

Abstract

The synthesis of 6 beta-bromopenicillanic acid labeled with deuterium and tritium in the beta-methyl group is described. The S-sulfoxide of benzyl- or p-methoxybenzyl 6 alpha-bromopenicillanate is refluxed in benzene containing an excess of tert-BuOD, D2O or HTO. After deoxygenation and deprotection of the ester, the labeled 6 alpha-bromopenicillanic acid is epimerized (N,O-bis(trimethylsilyl)acetamide/1,5-diazabicyclo[4.3.0]non-5-ene in CH2Cl2). The two epimers are separated by column chromatography.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chemical Phenomena
Chemistry
Deuterium
Isomerism
Penicillanic Acid / chemical synthesis*
Tritium

Substances

Tritium
brobactam
Penicillanic Acid
Deuterium