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S-adenosylhomocysteine analogues with the carbon-5' and sulfur atoms replaced by a vinyl unit.

ABSTRACT: Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo)vinyl analogue. [structure: see text]

SUBMITTER: Andrei D

PROVIDER: S-EPMC2532837 | biostudies-literature | 2006 Oct

REPOSITORIES: biostudies-literature

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S-adenosylhomocysteine analogues with the carbon-5' and sulfur atoms replaced by a vinyl unit.

Andrei Daniela D Wnuk Stanislaw F SF

Organic letters 20061001 22

Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo)vinyl analogue. [structure: see text] ...[more]

PMID: 17048851

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