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Issue 24, 2001
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Synthesis of the organic ligand of the molybdenum cofactor, in protected form

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Abstract

The organic ligand of the cofactor of the oxomolybdoenzymes has been synthesised in the protected and masked form, 5. The key steps in the conversion of the previously prepared 3, a protected 5-(2-amino-4-oxopteridin-6-yl)-4-(1,2-dihydroxyethyl)-1,3-dithiol-2-one were: formation of the pyran ring by reaction with a chloroformate giving a protected 8-amino-4-hydroxymethyl-6-(alkyloxycarbonyl)-5a,6,9,10-tetrahydro-[1,3]dithiolo[4′,5′:4,5]pyrano[3,2-g]pteridine-2,10-dione, 10, cyanoborohydride reduction of the 11,11a-imine, protection at N-11, and finally conversion of the alcohol into a protected phosphate giving 5.

Graphical abstract: Synthesis of the organic ligand of the molybdenum cofactor, in protected form

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Article information


Submitted
20 Sep 2001
Accepted
26 Oct 2001
First published
16 Nov 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 3239-3244
Article type
Paper

Synthesis of the organic ligand of the molybdenum cofactor, in protected form

B. Bradshaw, A. Dinsmore, W. Ajana, D. Collison, C. D. Garner and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 2001, 3239
DOI: 10.1039/B108579B

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