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A robust synthesis of 7,8-didemethyl-8-hydroxy-5-deazariboflavin.

ABSTRACT: The biosynthetic precursor of redox cofactor F420, 7,8-didemethyl-8-hydroxy-5-deazariboflavin, was prepared in four steps from 6-chlorouracil, 2-chloro-4-hydroxybenzaldehyde and bis-isopropylidene protected D-ribose. The latter aldehyde was transformed to the corresponding protected ribitylamine via the oxime, which was submitted to reduction with LiAlH4. Key advantage compared to previous syntheses is the utilization of a polyol-protective group which allowed the chromatographic purification of a key-intermediate product providing the target compound with high purity.

SUBMITTER: Bender M

PROVIDER: S-EPMC4901869 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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A robust synthesis of 7,8-didemethyl-8-hydroxy-5-deazariboflavin.

Bender Matthias M Mouritsen Henrik H Christoffers Jens J

Beilstein journal of organic chemistry 20160506

The biosynthetic precursor of redox cofactor F420, 7,8-didemethyl-8-hydroxy-5-deazariboflavin, was prepared in four steps from 6-chlorouracil, 2-chloro-4-hydroxybenzaldehyde and bis-isopropylidene protected D-ribose. The latter aldehyde was transformed to the corresponding protected ribitylamine via the oxime, which was submitted to reduction with LiAlH4. Key advantage compared to previous syntheses is the utilization of a polyol-protective group which allowed the chromatographic purification of ...[more]

PMID: 27340481

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