The isolation and absolute configuration of (1S,2S,3R)-4- Hydroxymethylcyclopent-4-ene-1,2,3-triol: A putative intermediate in the biosynthesis of aristeromycin by Streptomyces citricolor

Roberts, Stanley M.; Thorpe, Andrew; Turner, Nicholas J.; Blows, William M.; Buss, Antony D.; Dawson, Michael J.; Noble, David; Rudd, Brian A. M.; Sidebottom, Phillip J.; Wall, Wilfred F.

doi:10.1016/s0040-4039(00)60621-4

Cited by 11 publications

(1 citation statement)

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“…A stereoselective reduction of the carbonyl group in 13 from the sterically accessible convex face by using DIBAL-H furnished 14 . The deprotected triol (1 S ,2 S ,3 R )-4-hydroxymethylcyclopent-4-ene-1,2,3-triol, an antipode of 14 , is itself a natural product isolated from Streptomyces citricolor and was shown to be an intermediate in the biosynthesis of 1 2 Formal Synthesis of Neplanocin A …”

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A Formal Total Synthesis of (±)-Neplanocin A

Khan

Rout

2007

J. Org. Chem.

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Stereoselective formal synthesis of (+/-)-neplanocin A from a cyclopentane derivative employing an elegant strategy involving reiterative usage of an already existing acetonide protecting group is reported. The acetonide protecting group that is carried forward intact right from the starting adduct to an advanced intermediate is shuffled around twice as in a "relay race" through the synthetic sequence, thus avoiding unnecessary employment of additional protecting groups.

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A Formal Total Synthesis of (±)-Neplanocin A

Khan

Rout

2007

J. Org. Chem.

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Five‐Membered Cyclitol Phosphate Formation by a myo‐Inositol Phosphate Synthase Orthologue in the Biosynthesis of the Carbocyclic Nucleoside Antibiotic Aristeromycin

et al. 2016

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Aristeromycin is a unique carbocyclic nucleoside antibiotic produced by Streptomyces citricolor. In order to elucidate its intriguing carbocyclic formation, we used a genome-mining approach to identify the responsible enzyme. In silico screening with known cyclitol synthases involved in primary metabolism, such as myo-inositol-1-phosphate synthase (MIPS) and dehydroqunate synthase (DHQS), identified a unique MIPS orthologue (Ari2) encoded in the genome of S. citricolor. Heterologous expression of the gene cluster containing ari2 with a cosmid vector in Streptomyces albus resulted in the production of aristeromycin, thus indicating that the cloned DNA region (37.5 kb) with 33 open reading frames contains its biosynthetic gene cluster. We verified that Ari2 catalyzes the formation of a novel five-membered cyclitol phosphate from d-fructose 6-phosphate (F6P) with NAD as a cofactor. This provides insight into cyclitol phosphate synthase as a member of the MIPS family of enzymes. A biosynthetic pathway to aristeromycin is proposed based on bioinformatics analysis of the gene cluster.

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H

Collins¹

1998

Dictionary of Carbohydrates

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The isolation and absolute configuration of (1S,2S,3R)-4- Hydroxymethylcyclopent-4-ene-1,2,3-triol: A putative intermediate in the biosynthesis of aristeromycin by Streptomyces citricolor

Cited by 11 publications

References 5 publications

A Formal Total Synthesis of (±)-Neplanocin A

A Formal Total Synthesis of (±)-Neplanocin A

Five‐Membered Cyclitol Phosphate Formation by a myo‐Inositol Phosphate Synthase Orthologue in the Biosynthesis of the Carbocyclic Nucleoside Antibiotic Aristeromycin

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