Synthetic Study of 1, 2, 3-Tri-O-Acetyl-5-Deoxy-D-Ribofuranose

Zhang, Jian-Ting; Chen, Shi Peng; Feng, Jun; Liu, Dong Wang; Tang, Lin; Wang, Xiao Ji; Huang, Shuang Ping

doi:10.4028/www.scientific.net/amr.781-784.1184

Cited by 2 publications

(2 citation statements)

References 4 publications

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“…Synthesis of 5-deoxyribose and 7-deoxysedoheptulose 5dR and [U- 13 C 5 ]-5dR 5 were synthesized in a four-step synthesis based on the literature (53,54) with an additional optimization. All synthetic intermediates shown in the reaction scheme (Fig.…”

Section: Methodsmentioning

confidence: 99%

A bioactive molecule made by unusual salvage of radical SAM enzyme byproduct 5-deoxyadenosine blurs the boundary of primary and secondary metabolism

Rapp

Rath

Kilian

et al. 2021

Journal of Biological Chemistry

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Edited by Chris Whitfield 5-Deoxyadenosine (5dAdo) is the byproduct of many radical S-adenosyl-L-methionine enzyme reactions in all domains of life. 5dAdo is also an inhibitor of the radical S-adenosyl-Lmethionine enzymes themselves, making it necessary for cells to construct pathways to recycle or dispose of this toxic metabolite. However, the specific pathways involved have long remained unexplored. Recent research demonstrated a growth advantage in certain organisms by using 5dAdo or intermediates as a sole carbon source and elucidated the corresponding salvage pathway. We now provide evidence using supernatant analysis by GC-MS for another 5dAdo recycling route. Specifically, in the unicellular cyanobacterium Synechococcus elongatus PCC 7942 (S. elongatus), the activity of promiscuous enzymes leads to the synthesis and excretion first of 5-deoxyribose and subsequently of 7-deoxysedoheptulose. 7-Deoxysedoheptulose is an unusual deoxy-sugar, which acts as an antimetabolite of the shikimate pathway, thereby exhibiting antimicrobial and herbicidal activity. This strategy enables organisms with small genomes and lacking canonical gene clusters for the synthesis of secondary metabolites, like S. elongatus, to produce antimicrobial compounds from primary metabolism and enzymatic promiscuity. Our findings challenge the view of bioactive molecules as sole products of secondary metabolite gene clusters and expand the range of compounds that microorganisms can deploy to compete for their ecological niche.

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Section: Methodsmentioning

confidence: 99%

A bioactive molecule made by unusual salvage of radical SAM enzyme byproduct 5-deoxyadenosine blurs the boundary of primary and secondary metabolism

Rapp

Rath

Kilian

et al. 2021

Journal of Biological Chemistry

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show abstract

“…5dR and [U-13 C5]-5dR 5 were synthesized in a four-step synthesis based on literature (Sairam et al, 2003;Zhang et al, 2013) with additional optimization. All synthetic intermediates shown in the reaction scheme ( Figure S5) were verified by thin layer chromatography (TLC), mass spectrometry and NMR.…”

Section: Chemical Synthesis Of 5-deoxyribose and 7-deoxysedoheptulosementioning

confidence: 99%

5-Deoxyadenosine Salvage by Promiscuous Enzyme Activity leads to Bioactive Deoxy-Sugar Synthesis inSynechococcus elongatus

Rapp

Rath²,

Kilian

et al. 2020

Preprint

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Abstract7-Deoxysedoheptulose is an unusual deoxy-sugar, which acts as antimetabolite of the shikimate pathway thereby exhibiting antimicrobial and herbicidal activity. It is produced by the unicellular cyanobacterium Synechococcus elongatus PCC 7942, which has a small, stream-lined genome, assumed to be free from gene clusters for secondary metabolite synthesis. In this study, we identified the pathway for the synthesis of 7-deoxysedoheptulose. It originates from 5-deoxyadenosine, a toxic byproduct of radical S-adenosylmethionine (SAM) enzymes, present in all domains of life. Thereby we identified a novel 5-deoxyadenosine salvage pathway, which first leads to the synthesis and excretion of 5-deoxyribose and subsequently of 7-deoxysedoheptulose. Remarkably, all reaction steps are conducted by promiscuous enzymes. This is a unique example for the synthesis of a bioactive compound without involving a specific gene cluster. This challenges the view on bioactive molecule synthesis by extending the range of possible compounds beyond the options predicted from secondary metabolite gene clusters.

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Synthetic Study of 1, 2, 3-Tri-O-Acetyl-5-Deoxy-D-Ribofuranose

Abstract: A practical synthetic route towards 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose is described, which started from D-ribose and proceeded through ketalization,esterification,reduction,hydrolysis and acetylation in more than 30% overall yield.

Cited by 2 publications

References 4 publications

A bioactive molecule made by unusual salvage of radical SAM enzyme byproduct 5-deoxyadenosine blurs the boundary of primary and secondary metabolism

A bioactive molecule made by unusual salvage of radical SAM enzyme byproduct 5-deoxyadenosine blurs the boundary of primary and secondary metabolism

5-Deoxyadenosine Salvage by Promiscuous Enzyme Activity leads to Bioactive Deoxy-Sugar Synthesis inSynechococcus elongatus

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