Convenient syntheses of l-glycero-d-manno-heptose and d-glycero-d-manno-heptose

Brimacombe, J. S.; Kabir, A. K. M. S.

doi:10.1016/s0008-6215(00)90316-1

Cited by 49 publications

(18 citation statements)

References 11 publications

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“…After reduction with diisobutylaluminium hydride and catalytic bishydroxylation of 70 and 74 with osmium tetroxide, respectively, separation of the isomers is feasible via benzoylation to separate the L-glycero-L-gulo derivative 71 from the D-glycero-D-manno-heptoside 72, or via acetylation to isolate the crystalline L-glycero-D-manno-heptoside derivative 76 " Fig. (14)" [134,135]. Although the number of steps is high, the procedure is reliable to give multi-gram amounts of the 1 and 2.…”

Section: B) Synthesis Of Heptose Phosphatesmentioning

confidence: 99%

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Kosma

2008

COC

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Heptoses are important higher-carbon sugars occurring in numerous structural variations in several domains of the bacterial cell wall, which are briefly summarized. Recent approaches towards the chemical and chemo-enzymatic synthesis of these microbial monosaccharides will be summarized as well as progress made in the elucidation of two major biochemical pathways involving the synthesis of heptose phosphates and nucleotide-activated heptoses.

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Section: B) Synthesis Of Heptose Phosphatesmentioning

confidence: 99%

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Kosma

2008

COC

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“…12, 17 For example, the synthesis of penta-acetyl glycero-β-D-manno-heptose-1-phosphate is accompanied by the formation of the α-anomer (penta-acetyl glycero-α-D-manno-heptose-1-phosphate), which must be separated from the desired β-anomer products. 13 This process of separation is time-consuming and must be done utilizing laborious separation techniques.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE

Wen

Williams

et al. 2014

Bioorganic & Medicinal Chemistry

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An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-D-glycero-β-D-manno-heptose (ADP-D, D-heptose) was reported using chemically synthesized D, D-heptose-7-phosphate and the ADP-D, D-heptose biosynthetic enzymes HldE and GmhB. Moreover, the result of investigating substrate specificity of the kinase action of HldE revealed that HldE had highly restricted substrate specificity towards structurally modified heptose-7-phosphate analogs.

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“…As an additional example of utilization in a synthetic route, we applied our setup and methodology within the established synthetic approach towards d - glycero - d - manno heptose 9 (Scheme 4) [34, 35], which is the biological precursor of 3 . The key intermediate 5 (derived from d -mannose in multiple steps) underwent OsO 4 mediated dihydroxylation to deliver dd - manno -isomer 6 as a mixture with the minor ll - gulo isomer 7 [34, 35].…”

Section: Demonstration Of Successful Upscaling To Multigram Quantitiesmentioning

confidence: 99%

“…The key intermediate 5 (derived from d -mannose in multiple steps) underwent OsO 4 mediated dihydroxylation to deliver dd - manno -isomer 6 as a mixture with the minor ll - gulo isomer 7 [34, 35]. This crude mixture of 6 and 7 was subjected to conditions analogous to above to achieve simultaneous acetonide cleavage (trans-acetalization) and concomitant trans-glycosylation under continuous flow conditions, thereby locking the targeted pyranose form.…”

Section: Demonstration Of Successful Upscaling To Multigram Quantitiesmentioning

confidence: 99%

Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing

Aronow¹,

Stanetty²,

Baxendale

et al. 2018

Monatsh Chem

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A continuous flow procedure for the synthesis of methyl glycosides (Fischer glycosylation) of various monosaccharides using a heterogenous catalyst has been developed. In-depth analysis of the isomeric composition was undertaken and high consistency with corresponding results observed under microwave heating was obtained. Even in cases where addition of water was needed to achieve homogeneity—a prerequisite for the flow experiments—no detrimental effect on the conversion was found. The scalability was demonstrated on a model case (mannose) and as part of the target-oriented synthesis of d-glycero-d-manno heptose, both performed on multigram scale.Graphical abstract Electronic supplementary materialThe online version of this article (10.1007/s00706-018-2306-8) contains supplementary material, which is available to authorized users.

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Convenient syntheses of l-glycero-d-manno-heptose and d-glycero-d-manno-heptose

Cited by 49 publications

References 11 publications

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE

Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing

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