72028-62-7

Basic information

• Product Name: METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE
• Synonyms: ALPHA-D-MAN-[1->3]-ALPHA-D-MAN-1->OME;METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE;METHYL 3-O-(A-D-MANNOPYRANOSYL)-A-D-MANNOPYRANOSIDE;MANNOSE ALPHA1,3-MANNOSE, ALPHA-METHYL GLYCOSIDE;MAN1-A-3MAN-A-OME;Mannose a1,3-Mannose, a-MethylGlycoside;methyl 3-O-A-D-mannopyranosyl-A-D-*mannopyranosid;methyl 3-o-α-d-mannopyranosyl-α-d-mannopyranoside
• CAS NO: 72028-62-7
• Molecular Formula: C₁₃H₂₄O₁₁
• Molecular Weight: 356.32
• Product Categories: Oligosaccharide Compounds;Oligosaccharides
• Mol File: 72028-62-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 169-174°C
• Boiling Point: 669.2 °C at 760 mmHg
• Flash Point: 358.5 °C
• Appearance: white crystalline solid
• Density: 1.63 g/cm³
• Vapor Pressure: 9.03E-21mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: −20°C
• Solubility: Methanol, Water
• Stability: Hygroscopic
• CAS DataBase Reference: METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE(72028-62-7)
• EPA Substance Registry System: METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE(72028-62-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 72028-62-7(Hazardous Substances Data)

Usage

Description

METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE is a white crystalline solid that is a derivative of a disaccharide, specifically a glycoside. It is composed of two sugar units, alpha-D-mannopyranosyl and alpha-D-mannopyranosyl, linked together. METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE is significant in the field of organic chemistry and biochemistry due to its unique structure and potential applications.

Uses

1. Used in Organic Synthesis:
METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE is used as a key intermediate in organic synthesis for the development of various complex organic molecules. Its unique structure allows for the creation of a wide range of compounds with potential applications in different industries.
2. Used in the Study of UDP-N-Acetylglucosamine:
METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE is also utilized in the study of UDP-N-Acetylglucosamine, an important molecule in the biosynthesis of peptidoglycan, a major component of bacterial cell walls. Understanding the role of this compound in the biosynthetic pathway can lead to the development of new antibiotics and antimicrobial agents.
3. Used in Pharmaceutical Research:
Given its unique structure and properties, METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE may have potential applications in the pharmaceutical industry. It could be used as a starting material for the development of new drugs targeting various diseases, including those related to carbohydrate metabolism and recognition.
4. Used in the Food Industry:
In the food industry, METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE could be used as a component in the development of novel sweeteners or flavor enhancers, taking advantage of its sugar-derived structure.
5. Used in Material Science:
METHYL 3-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE's unique structure may also find applications in material science, particularly in the development of new polymers or materials with specific properties, such as improved biodegradability or enhanced mechanical strength.

InChI:InChI=1/C13H24O11/c1-21-12-10(20)11(7(17)5(3-15)22-12)24-13-9(19)8(18)6(16)4(2-14)23-13/h4-20H,2-3H2,1H3/t4-,5-,6-,7-,8+,9+,10+,11+,12+,13-/m1/s1

Upstream product

• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 20750-02-1 methyl 2-O-acetyl-4,6-O-benzylidene-β,D-glucopyranoside 
• 67-56-1 methanol 
• 195715-87-8 Acetic acid (2R,3R,4S,5R,6S)-5-acetoxy-2-acetoxymethyl-6-fluoro-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 66583-05-9 methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 709-50-2 methyl beta-D-glucopyranoside 
• 23202-66-6 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide 
• 68036-18-0 1,2,4,6-tetra-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranose 
• 29842-30-6 laminarihexaose 
• 3256-04-0 laminaritriose 
• 26212-72-6 laminaritetraose 
• 23743-55-7 laminaripentaose 
• 59-56-3 α-D-glucopyranosyl-1-phosphate 

Downstream Products

• 78797-77-0 methyl 2,4-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranosyl)-6-O-trityl-β-D-glucopyranoside 
• 78797-79-2 methyl 2,4-di-O-acetyl-6-O-p-tolylsulfonyl-3-O-(2,3,4-tri-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranosyl)-β-D-glucopyranoside 

Relevant articles and documents

Synthesis and structural investigation of a series of mannose-containing oligosaccharides using mass spectrometry

A series of compounds associated with naturally occurring and biologically relevant glycans consisting of α-mannosides were prepared and analyzed using collision-induced dissociation (CID), energy-resolved mass spectrometry (ERMS), and 1H nucle

Characterization of a bacterial laminaribiose phosphorylase

Bacterial laminaribiose phosphorylase (LBPbac) was first identified and purified from cell-free extract of Paenibacillus sp. YM-1. It phosphorolyzed laminaribiose into α-glucose 1-phosphate and glucose, but did not phosphorolyze other glucobioses. It slightly phosphorolyzed laminaritriose and higher laminarioligosaccharides. The specificity of the degree of polymerization of the substrate was clearly different from that of the enzyme of Euglena gracilis (LBPEug): LBPbac was more specific to laminaribiose than LBPEug. It showed acceptor specificity in reverse phosphorolysis similar to LBPEug. Cloning of the gene encoding LBPbac (lbpA) has revealed that LBPbac is a member of the glucoside hydrolase family 94, which includes cellobiose phosphorylase, cellodextrin phosphorylase, and N,N0-diacetylchitobiose phosphorylase. The genes that encode the components of an ATP-binding cassette sugar transporter specific to laminarioligosaccharides were identified upstream of lbpA, suggesting that the role of LBPbac is to utilize laminaribiose generated outside the cell. This role is different from that of LBPEug, which participates in the utilization of paramylon, the intracellular storage 1,3-β-glucan.

Thermus thermophilus glycosynthases for the efficient synthesis of galactosyl and glucosyl β-(1→3)-glycosides

Inverting mutant glycosynthases were designed according to the Withers strategy, starting from wild-type Thermus thermophilus retaining Tt-β-Gly glycosidase. Directed mutagenesis of catalytic nucleophile glutamate 338 by alanine, serine, and glycine afforded the E338A, E338S, and E338G mutant enzymes, respectively. As was to be expected, the mutants were unable to catalyze the hydrolysis of the transglycosidation products. In agreement with previous results, the E338S and E338G catalysts were much more efficient than E338A. Moreover, our results showed that these enzymes were inactive in the hydrolysis of the α-D-glycopyranosyl fluorides used as donors, and so suitable experimental conditions, under which the rate of spontaneous hydrolysis of the donor was considerably lower than that of enzymatic transglycosidation, provided galactosyl and glucosyl β-(1→3)-glycosides in yields of up to 90%. The structure of native Tt-β-Gly available in the Protein Data Bank offers a good basis for interpretation of our results by means of molecular modeling. Thus, in the case of the E338S mutant, a lower energy of the system was obtained when the donor and the acceptor were in the right position to form the β-(1→3)-glycosidic bond. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.