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226988-19-8

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226988-19-8 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 226988-19-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,2,6,9,8 and 8 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 226988-19:
(8*2)+(7*2)+(6*6)+(5*9)+(4*8)+(3*8)+(2*1)+(1*9)=178
178 % 10 = 8
So 226988-19-8 is a valid CAS Registry Number.

226988-19-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name (-)-1-Azafagomine

1.2 Other means of identification

Product number -
Other names (-)-1-azafagomine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:226988-19-8 SDS

226988-19-8Relevant articles and documents

Advances in the synthesis of homochiral (-)-1-azafagomine and (+)-5-epi-1-azafagomine. 1-N-phenyl carboxamide derivatives of both enantiomers of 1-azafagomine: Leads for the synthesis of active α-glycosidase inhibitors.

Alves, M. Jose,Costa, Flora T.,Duarte, Vera C. M.,Fortes, Antonio Gil,Martins, Jose A.,Micaelo, Nuno M.

scheme or table, p. 9584 - 9592 (2012/01/03)

A new expeditious preparation of homochiral ( - )-1-azafagomine and (+)-5-epi-1-azafagomine has been devised. Stoodley's diastereoselective cycloaddition of dienes bearing a 2,3,4,6-tetraacetyl glucosyl chiral auxiliary to 4-phenyl-1,2,4-triazole-3,5-dione was merged with Bols's protocol for functionalizing alkenes into molecules bearing a glucosyl framework. Homochiral (+)-5-epi-1-azafagomine was synthetized for the first time. Partial reductive cleavage of the phenyltriazolidinone moiety afforded new homochiral 1-N-phenyl carboxamide derivatives of 1-azafagomine. Both enantiomers of these derivatives were synthetized and tested, displaying a very good enzymatic inhibition toward baker's yeast α-glucosidase. The molecular recognition mechanism of the 1-N-phenyl carboxamide derivative of 1-azafagomine by α-glucosidase from baker's yeast was studied by molecular modeling. The efficient packing of the aromatic ring of the 1-N-phenyl carboxamide moiety into a hydrophobic subsite (pocket) in the enzyme's active site seems to be responsible for the improved binding affinity in relation to underivatized ( - )-1-azafagomine and (+)-1-azafagomine.

Enantiospecific synthesis of 1-azafagomine

Ernholt,Thomsen,Lohse,Plesner,Jensen,Hazell,Liang,Jakobsen,Bols

, p. 278 - 287 (2007/10/03)

For the first time the two enantiomeric forms of the glycosidase inhibitor 1-azafagomine have been synthesised starting from D- and L-xylose. D-Xylose was converted to the 2,3,5-tribenzylfuranose, which upon reductive amination with tert-butyl carbazate gave the protected 1-hydrazino-1- deoxypentitol in high yield. N-acetylation, mesylation of the 4-OH, removal of the Boc group, cyclisation and deprotection gave (+)-1-azafagomine ((+)- 1). By a similar sequence of reactions, L-xylose was converted to (-)-1- azafagomine ((-)1). Enzymatic and other routes to optically pure 1- azafagomine were also studied. Compound (-)-1 is a potent competitive glycosidase inhibitor, while (+)-1 has no biological activity. The inhibition of almond β-glucosidase by (-)-1 was found to be slow owing to a slow binding step of inhibitor to enzyme, with no subsequent conformational rearrangement. The rate constants for binding and release were found to be 3.3 x 104 M-1 s-1 and 0.011 s-1, respectively, yielding K(i) = 0.33 μM.

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