120104-31-6

Basic information

• Product Name: (2S,4S,5R,6R)-2,4,5-Trihydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
• Synonyms: (2S,4S,5R,6R)-2,4,5-Trihydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
• CAS NO: 120104-31-6
• Molecular Weight: 268.221
• Mol File: 120104-31-6.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (2S,4S,5R,6R)-2,4,5-Trihydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S,5R,6R)-2,4,5-Trihydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid(120104-31-6)
• EPA Substance Registry System: (2S,4S,5R,6R)-2,4,5-Trihydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid(120104-31-6)

Safety Data

• Hazardous Substances Data: 120104-31-6(Hazardous Substances Data)

Upstream product

• 3458-28-4 D-Mannose 
• 113-24-6 sodium pyruvate 
• 78082-66-3 (methyl 3-deoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onic acid 
• 138913-32-3 (3aS,4R,5R,7aS)-7-chloro-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol 
• 188854-96-8 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonic acid 
• 129385-09-7 methyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-(anti/syn-N-nitrosoacetamido)-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 
• 78082-65-2 methyl (methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 
• 78082-67-4 methyl (methyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 41521-03-3 methyl [methyl 4,7,8,9-tetra-O-acetyl-5-acetamido-3,5-dideoxy-β-D-glycero-D-galacto-non-2-ulopyranoside]onate 
• 154796-73-3 (methyl 4,5,7,8,9-penta-O-benzyl-3-deoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onic acid 
• 154796-72-2 methyl 4,5,7,8,9-penta-O-benzyl-3-deoxy-β-D-glycero-D-galacto-2-nonosulopyranoside 
• 209117-87-3 (S)-4-{(4R,5R)-2,2-Dimethyl-5-[(1S,2R)-1,2,3-tris-(tert-butyl-dimethyl-silanyloxy)-propyl]-[1,3]dioxolan-4-yl}-4-hydroxy-2-methylene-butyric acid ethyl ester 
• 209117-85-1 (4S,5R)-2,2-Dimethyl-5-[(1S,2R)-1,2,3-tris-(tert-butyl-dimethyl-silanyloxy)-propyl]-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 209117-86-2 (4S,5R)-2,2-Dimethyl-5-[(1S,2R)-1,2,3-tris-(tert-butyl-dimethyl-silanyloxy)-propyl]-[1,3]dioxolane-4-carbaldehyde 

Downstream Products

• 1239945-63-1 C₁₇H₂₀O₁₀ 
• 1239945-64-2 C₁₈H₁₈O₁₁ 
• 112543-66-5 3-deoxy-D-glycero-D-galacto-nonulosonic acid ammonium salt 

Relevant articles and documents

Glycoside cleavage by a new mechanism in unsaturated glucuronyl hydrolases

Unsaturated glucuronyl hydrolases (UGLs) from GH family 88 of the CAZy classification system cleave a terminal unsaturated sugar from the oligosaccharide products released by extracellular bacterial polysaccharide lyases. This pathway, which is involved in extracellular bacterial infection, has no equivalent in mammals. A novel mechanism for UGL has previously been proposed in which the enzyme catalyzes hydration of a vinyl ether group in the substrate, with subsequent rearrangements resulting in glycosidic bond cleavage. However, clear evidence for this mechanism has been lacking. In this study, analysis of the products of UGL-catalyzed reactions in water, deuterium oxide, and dilute methanol in water, in conjunction with the demonstration that UGL rapidly cleaves thioglycosides and glycosides of inverted anomeric configuration (substrates that are resistant to hydrolysis by classical glycosidases), provides strong support for this new mechanism. A hydration-initiated process is further supported by the observed UGL-catalyzed hydration of a C-glycoside substrate analogue. Finally, the observation of a small β-secondary kinetic isotope effect suggests a transition state with oxocarbenium ion character, in which the hydrogen at carbon 4 adopts an axial geometry. Taken together, these observations validate the novel vinyl ether hydration mechanism and are inconsistent with either inverting or retaining direct hydrolase mechanisms at carbon 1.

A Concise Chemical Synthesis of (+)-3-Deoxy-D-glycero-D-galacto-nonulosonic acid (KDN)

The sialic acid KDN is synthesized stereoselectively in three steps from D-mannose by taking advantage of an indium mediated coupling reaction in aqueous medium.

Microbial glycosyltransferases for carbohydrate synthesis: α-2,3-sialyltransferase from Neisseria gonorrheae

The α-2,3-sialyltransferase from Neisseria gonorrheae was overproduced in E. coli for exploitation of its substrate specificity and synthetic utility. Several potential acceptor substrates were synthesized in this study, including mono- and oligosaccharid

First total synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) from a non-carbohydrate source

Enantiopure cis-1,2-dihydrocatechol 2, a product obtained by microbial oxidation of chlorobenzene, has been converted into KDN 1 via a ten step reaction sequence.