Synthesis of Valiolamine and Some Precursors for Bioactive Carbaglycosylamines from (−)-<i>vibo</i>-Quercitol Produced by Biogenesis of <i>myo</i>-Inositol

Ogawa, Seiichiro; Kanto, Miki

doi:10.1021/np068069t

Cited by 24 publications

(5 citation statements)

References 25 publications

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“…In addition, a single regioisomer was obtained as a result of nucleophilic attack at the allylic position of the acetoxonium ion (Scheme ). The same mechanism has also been observed in the synthesis of (–)‐1‐epi‐valiolamine from a tosylate precursor bearing a trans ‐α‐acetoxy group 22,91…”

Section: Treatment Of Cyclitol Derivatives With Nitrogen Nucleophilessupporting

confidence: 62%

Recent Advances in the Chemistry of Aminocyclitols

Delgado

2008

Eur J Org Chem

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Keywords: Aminocyclitols / Cyclitols / Natural products / Synthetic methodology / Stereocontrol / Disatereoselectivity / Functional group interconversion Aminocyclitols are a group of natural products with remarkable biological activities. Over the last years, significant efforts have been made to develop synthetic methodologies directed not only towards their total synthesis but also towards the design of structural analogues with improved or novel biological properties. The aim of this review is to provide the reader with a concise update of the most relevant methods for the synthesis of aminocyclitols described in the literature.

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Section: Treatment Of Cyclitol Derivatives With Nitrogen Nucleophilessupporting

confidence: 62%

Recent Advances in the Chemistry of Aminocyclitols

Delgado

2008

Eur J Org Chem

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“…Because VQ was produced from DOI, this novel enzymatic pathway also provides a cost-effective method to synthesize DOI, as well as various DOI-derived chemicals, such as scyllo-quercitol, 2-deoxystreptamine-containing aminoglycoside antibiotics (Ota et al, 2000), aromatic compounds (Ota et al, 2000), and carbasugar derivatives (Ogawa & Kanto, 2007). We also demonstrated VQ production from high concentrations of substrates and obtained a final VQ concentration of 25.3 g/L with a purity of 87%, indicating the industrial scale-up potential for VQ production.…”

Section: Discussionmentioning

confidence: 99%

“…We also demonstrated VQ production from high concentrations of substrates and obtained a final VQ concentration of 25.3 g/L with a purity of 87%, indicating the industrial scale-up potential for VQ production. Because VQ was produced from DOI, this novel enzymatic pathway also provides a cost-effective method to synthesize DOI, as well as various DOI-derived chemicals, such as scyllo-quercitol, 2-deoxystreptamine-containing aminoglycoside antibiotics (Ota et al, 2000), aromatic compounds (Ota et al, 2000), and carbasugar derivatives (Ogawa & Kanto, 2007).…”

Section: Discussionmentioning

confidence: 99%

Facile synthesis of (−)‐vibo‐quercitol from maltodextrin via an in vitro synthetic enzymatic biosystem

Bai

Meng

Wei

et al. 2019

Biotech & Bioengineering

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vibo-Quercitol (VQ: 1L-1,2,4/3,5-cyclohexanepentol), a form of deoxyinositol, is an alternative chiral building block in the synthesis of bioactive compounds to control diabetes. In this study, an adenosine triphosphate-free in vitro synthetic enzymatic biosystem composed of five enzymes (including one enzyme for NADH regeneration) was constructed to produce VQ from maltodextrin in one-pot. After optimization of reaction conditions, 7.6 g/L VQ was produced from 10 g/L maltodextrin with a product yield (mol/mol) of 77%, and 25.3 g/L VQ with a purity of 87% was produced from 50 g/L maltodextrin through simple scaling up of this nonfermentative enzymatic biosystem. Therefore, this study provides an economical and environmentally friendly method for the envisioned quercitol biosynthesis.

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“…To facilitate the accessibility of N -alkyl-carbaglycosylamines, an improved and practical synthetic route to chiral carbaglycosylamines from myo -inositol ( 4 ) has been established. 34 ) Both NOV ( 26 ) and NOEV ( 27 ) have later been found to possess chaperone activity for mutant forms of their target glycosidases. Since then, it has become of interest to develop carbaglycosylamine-based pharmacological chaperones for lysosomal glycosidases associated with lysosomal storage disorders (LSDs).…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of biologically active carbaglycosylamines: From glycosidase inhibitors to pharmacological chaperones

Ogawa

Kuno

Toyokuni

2022

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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For over 50 years, our group has been involved in synthetic studies on biologically active cyclitols including carbasugars. Among a variety of compounds synthesized, this review focuses on carbaglycosylamine glycosidase inhibitors, highlighting the following: (1) the naturally occurring N -linked carbaoligosaccharide α-amylase inhibitor acarbose and related compounds; (2) the novel synthetic β-glycosidase inhibitors, 1′- epi -acarviosin and its 6-hydroxy analogue as well as β-valienaminylceramide and its 4′-epimer; (3) the discovery of the β-glycosidase inhibitors with chaperone activity, N -octyl-β-valienamine (NOV) and its 4-epimer (NOEV); and (4) the recent development of the potential pharmacological chaperone N -alkyl-conduramine F-4 derivatives.

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Synthesis of Valiolamine and Some Precursors for Bioactive Carbaglycosylamines from (−)-vibo-Quercitol Produced by Biogenesis of myo-Inositol

Abstract: A convenient and practical synthesis of valiolamine (4) and its related carbaglycosylamine glycosidase inhibitors from (-)-vibo-quercitol (13), a compound readily produced by biogenesis of myo-inositol (9), is described.

Cited by 24 publications

References 25 publications

Recent Advances in the Chemistry of Aminocyclitols

Recent Advances in the Chemistry of Aminocyclitols

Facile synthesis of (−)‐vibo‐quercitol from maltodextrin via an in vitro synthetic enzymatic biosystem

Design and synthesis of biologically active carbaglycosylamines: From glycosidase inhibitors to pharmacological chaperones

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