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Total synthesis of geranylgeranylglyceryl phosphate enantiomers: substrates for characterization of 2,3-O-digeranylgeranylglyceryl phosphate synthase.

ABSTRACT: To determine the enantioselectivity of (S)-2,3-di-O-geranylgeranylglyceryl phosphate synthase (DGGGPS) from the thermoacidophilic archaeon Sulfolobus solfataricus, we developed an efficient enantioselective route to the enantiomeric geranylgeranylglyceryl phosphates (R)-GGGP and (S)-GGGP. Previous routes to these substrates involved enzymatic conversions due to the lability of the polyprenyl chains toward common phosphorylation reaction conditions. The synthesis described herein employs a mild trimethyl phosphite/carbon tetrabromide oxidative phosphorylation to circumvent this problem. In contrast to previous results suggesting that only (S)-GGGP can act as the prenyl acceptor substrate, both (R)-GGGP and (S)-GGGP were found to be substrates for DGGGPS.

SUBMITTER: Zhang H

PROVIDER: S-EPMC2543118 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature

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Total synthesis of geranylgeranylglyceryl phosphate enantiomers: substrates for characterization of 2,3-O-digeranylgeranylglyceryl phosphate synthase.

Zhang Honglu H Shibuya Kyohei K Hemmi Hisashi H Nishino Tokuzo T Prestwich Glenn D GD

Organic letters 20060301 5

To determine the enantioselectivity of (S)-2,3-di-O-geranylgeranylglyceryl phosphate synthase (DGGGPS) from the thermoacidophilic archaeon Sulfolobus solfataricus, we developed an efficient enantioselective route to the enantiomeric geranylgeranylglyceryl phosphates (R)-GGGP and (S)-GGGP. Previous routes to these substrates involved enzymatic conversions due to the lability of the polyprenyl chains toward common phosphorylation reaction conditions. The synthesis described herein employs a mild t ...[more]

PMID: 16494480

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