Synthesis and glycosidase inhibitory activity of some N -Substituted 6-Deoxy-5a-carba-β- dl - and l -galactopyranosylamines

Ogawa, Seiichiro; Fujieda, Shigeo; Sakata, Yoko; Ishizaki, Masahiro; Hisamatsu, Seiichi; Okazaki, Kensuke

doi:10.1016/s0960-894x(03)00742-x

Cited by 17 publications

(5 citation statements)

References 8 publications

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“…This activity appeared to be associated with the D-enantiomers exclusively, that is, N-alkyl-6-deoxy-5a-carbaβ-D-galactopyranosylamines (D-119). 118 Carbasugar derivatives have also been envisaged to play roles in elucidating and controlling other biological events that involve sugar moieties. This includes the synthesis of analogues of enzyme substrates, which were modified by replacing part of their structures with carbasugar units and which were expected to be used in the elucidation of the mode of action of sugar transferases.…”

Section: Biological Activity Of Carbapyranosesmentioning

confidence: 99%

“…In a similar manner, compounds (±)- 119a − g , prepared by chemical modification of (±)- 117 , showed very strong inhibitory activity toward both β-galactosidase and β-glucosidase enzymes with no specificity associated with the 4-epimeric structures. This activity appeared to be associated with the d -enantiomers exclusively, that is, N -alkyl-6-deoxy-5a-carba-β- d -galactopyranosylamines ( d - 119 ) 29 Carbafucopyranosylamines as hydrolase inhibitors (when racemic, only l -enantiomers are shown). …”

Section: 2 Biological Activity Of Carbapyranosesmentioning

confidence: 99%

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Synthesis and Conformational and Biological Aspects of Carbasugars

et al. 2007

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Section: Biological Activity Of Carbapyranosesmentioning

confidence: 99%

Section: 2 Biological Activity Of Carbapyranosesmentioning

confidence: 99%

Synthesis and Conformational and Biological Aspects of Carbasugars

et al. 2007

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“…Deprotection of diol 10 with ferric chloride in dichloromethane gave tetrol 11 , which is an olefin analogue of cyclophellitol. Several carbasugars have previously shown good inhibition of glycosidases, and we speculated if 11 would be a reversible inhibitor. Thus, compound 11 was tested against yeast α-glucosidase, almond β-glucosidase, green coffee bean α-galactosidase, Escherichia coli β-galactosidase, and Jack bean α-mannosidase .…”

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confidence: 99%

A Short Synthesis of (+)-Cyclophellitol

2005

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[reaction: see text] A new synthesis of (+)-cyclophellitol, a potent beta-glucosidase inhibitor, has been completed in nine steps from D-xylose. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 5-deoxy-5-iodo-xylofuranoside followed by a highly diastereoselective indium-mediated coupling with ethyl 4-bromocrotonate. Subsequent ring-closing olefin metathesis, ester reduction, olefin epoxidation, and deprotection then afford the natural product. This constitutes the shortest synthesis of (+)-cyclophellitol reported to date.

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“…In a similar manner, chemical modifications of 168 generated N-substituted derivatives (±)-170a-g, which were found to be very strong -galactosidase as well asglucosidase inhibitors with no specificity associated with the 4-epimeric structures. This inhibitory activity appeared attributable to D-enantiomers exclusively, that is, N-alkyl-6-deoxy-5a-carba--D-galactopyranosylamines (D-170) [360] ( Figure 29). Carbasugar derivatives have also been envisaged to play roles in elucidating and controlling other biological events that involve sugar moieties.…”

Section: International Journal Of Carbohydrate Chemistrymentioning

confidence: 99%

Biosynthesis and Biological Activity of Carbasugars

Roscales

Plumet

2016

International Journal of Carbohydrate Chemistry

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The first synthesis of carbasugars, compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene moiety, was described in 1966 by Professor G. E. McCasland's group. Seven years later, the first true natural carbasugar (5a-carba-R-D-galactopyranose) was isolated from a fermentation broth of Streptomyces sp. MA-4145. In the following decades, the chemistry and biology of carbasugars have been extensively studied. Most of these compounds show interesting biological properties, especially enzymatic inhibitory activities, and, in consequence, an important number of analogues have also been prepared in the search for improved biological activities. The aim of this review is to give coverage on the progress made in two important aspects of these compounds: the elucidation of their biosynthesis and the consideration of their biological properties, including the extensively studied carbapyranoses as well as the much less studied carbafuranoses.

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Synthesis and glycosidase inhibitory activity of some N -Substituted 6-Deoxy-5a-carba-β- dl - and l -galactopyranosylamines

Cited by 17 publications

References 8 publications

Synthesis and Conformational and Biological Aspects of Carbasugars

Synthesis and Conformational and Biological Aspects of Carbasugars

A Short Synthesis of (+)-Cyclophellitol

Biosynthesis and Biological Activity of Carbasugars

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