Studies on the Biodegradation of Fosfomycin: Synthesis of 13C-Labeled Intermediates, Feeding Experiments with Rhizobium huakuii PMY1, and Isolation of Labeled Amino Acids from Cell Mass by HPLC

被引：5

作者：

McGrath, John W. ^{[2
]}

Hammerschmidt, Friedrich ^{[1
]}

Kaehlig, Hanspeter ^{[1
]}

Wuggenig, Frank ^{[1
]}

Lamprecht, Guenther ^{[3
]}

Quinn, John P. ^{[2
]}

机构：

[1] Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria

[2] Queens Univ Belfast, Sch Biol Sci, Ctr Med Biol, Belfast BT9 7BL, Antrim, North Ireland

[3] Univ Vienna, Inst Analyt Chem, A-1090 Vienna, Austria

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 47期

基金：

奥地利科学基金会;

关键词：

amino acids; biotransformations; fosfomycin; hydroxyacetone; isotopic labeling; P-C BOND; MICROBIAL-METABOLISM; NATURAL-PRODUCTS; BIOSYNTHESIS; MECHANISM; ACETATE; INSIGHT; OXIRANE;

D O I：

10.1002/chem.201100725

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Racemic (1R*,2R*)-1,2-dihydroxy-[1-13C1]propylphosphonic acid and 1-hydroxy-[1-13C1]acetone were synthesized and fed to R. huakuii PMY1. Alanine and a mixture of valine and methionine were isolated as their N-acetyl derivatives from the cell hydrolysate by reversed-phase HPLC and analyzed by NMR spectroscopy. It was found that the carbon atoms of the respective carboxyl groups were highly 13C-labeled (up to 65?%). Hydroxyacetone is therefore considered an obligatory intermediate of the biodegradation of fosfomycin by R. huakuii PMY1.

引用

页码：13341 / 13348

页数：8

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