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S-Ribosylhomocysteine Analogues Modified at the Ribosyl C-4 Position

S-Ribosylhomocysteine Analogues Modified at the Ribosyl C-4 Position

Christiane Chbib, Adam J Sobczak, Mukesh Mudgal, Cesar Gonzalez, Daniel Lumpuy, Justyna Nagaj, Kamila Stokowa-Soltys, Stanislaw F Wnuk

J Sulphur Chem. 2016;37(3):307-327.

PMID: 27516805

Abstract:

4-C-Alkyl/aryl-S-ribosylhomocysteine (SRH) analogues were prepared by coupling of homocysteine with 4-substituted ribofuranose derivatives. The diastereoselective incorporation of the methyl substituent into the 4 position of the ribose ring was accomplished by addition of methylmagnesium bromide to the protected ribitol-4-ulose yielding the 4-C-methylribitol in 85% yield as single 4R diastereomer. The 4-C hexyl, octyl, vinyl, and aryl ribitols were prepared analogously. Chelation controlled addition of a carbanion to ketones from the (Si-face) was responsible for the observed stereochemical outcome. Oxidation of the primary alcohol of the 4-C ribitols with the catalytic amount of tetrapropylammonium perruthenate in the presence of N-methylmorpholine N-oxide produced 4-C-alkylribono-1,4-lactones in high yields. Mesylation of the latter compounds at the 5-hydroxyl position and treatment with a protected homocysteine thiolate afforded protected 4-C-alkyl/aryl-SRH analogues as the lactones. Reduction with lithium triethylborohydride and successive global deprotections with TFA afforded 4-C-alkyl/aryl SRH analogues. These analogues might impede the S-ribosylhomocysteinase(LuxS)-catalyzed reaction by preventing β-elimination of a homocysteine molecule, and thus depleting the production of quorum sensing signaling molecule AI-2.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP114615826	Tetrapropylammonium perruthenate		114615-82-6	Price

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