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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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Publication details

The article was received on 20 Sep 2001, accepted on 26 Oct 2001 and first published on 16 Nov 2001


Article type: Paper
DOI: 10.1039/B108579B
J. Chem. Soc., Perkin Trans. 1, 2001, 3239-3244

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    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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