39937-91-2

Basic information

• Product Name: 2-deoxy-2,3-didehydro-N-glycoloylneuraminic acid
• Synonyms: 2-deoxy-2,3-didehydro-N-glycoloylneuraminic acid
• CAS NO: 39937-91-2
• Molecular Formula: C11H17NO9
• Molecular Weight: 307.25398
• Mol File: 39937-91-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 854.4°Cat760mmHg
• Flash Point: 470.5°C
• Appearance: /
• Density: 1.69g/cm³
• Vapor Pressure: 5.47E-34mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 2-deoxy-2,3-didehydro-N-glycoloylneuraminic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-deoxy-2,3-didehydro-N-glycoloylneuraminic acid(39937-91-2)
• EPA Substance Registry System: 2-deoxy-2,3-didehydro-N-glycoloylneuraminic acid(39937-91-2)

Safety Data

• Hazardous Substances Data: 39937-91-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H17NO9/c13-2-5(16)9(18)10-8(12-7(17)3-14)4(15)1-6(21-10)11(19)20/h1,4-5,8-10,13-16,18H,2-3H2,(H,12,17)(H,19,20)/t4-,5+,8+,9+,10+/m0/s1

Upstream product

• 1454818-68-8 ammonium 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate 
• 13831-31-7 Acetoxyacetyl chloride 
• 72-87-7 N-acetyl-D-mannosamine 
• 24967-27-9 2,3-dehydro-2-deoxy-N-acetylneuraminic acid 
• 41976-42-5 5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid 
• 18409-13-7 3'-sialyllactose 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 

Relevant articles and documents

SIALIDASE INHIBITORS AND PREPARATION THEREOF

New 2-deoxy-2,3-dehydro-sialic acids and 2,7-anhydro-sialic acids, which are useful as sialidase inhibitors, and enzymatic methods for preparing them are disclosed. The methods include forming a reaction mixture comprising a glycoside acceptor, a sialic acid donor, and a sialyltransferase; maintaining the reaction mixture under conditions sufficient to form a sialoside; and contacting the sialoside with a Streptococcus pneumoniae sialidase to form the sialic acid product. Methods for the inhibition and sialidases and the treatment of cancer and infectious diseases are also disclosed.

The design, synthesis and biological evaluation of neuraminic acid-based probes of Vibrio cholerae sialidase

A molecular modelling study using the program GRID has been used to investigate the structural requirements of a potential inhibitor binding to Vibrio cholerae sialidase. A number of favourable interactions were predicted between the sialidase and Neu2en derivatives containing hydroxyl- or halogen-substituted acyl groups on the C-5 amine. As a result of this study, a detailed analysis of the interactions of C-5-substituted Neu2en derivatives with the active site of V. cholerae sialidase was undertaken using a conformational searching routine based on molecular dynamics. Based on the results of these molecular design studies several N-acyl-Neu2en-based probes were prepared and evaluated for sialidase inhibition. As envisaged, and pleasingly, the designed compounds were found to be accommodated by the enzyme's active site architecture, and to be strong inhibitors of V. cholerae sialidase. Copyright (C) 2000 Elsevier Science Ltd.