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

• 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 
• 3162-96-7 methyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 3254-15-7 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 125365-19-7 methyl 2-O-acetyl-4,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-<*>-galactopyranosyl)-α-<*>-mannopyranoside 
• 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 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 125365-18-6 Methyl 2-O-allyl-4,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-<*>-galactopyranosyl)-α-<*>-mannopyranoside 
• 219313-07-2 Methyl 2-O-allyl-4,6-di-O-benzyl-α-[*]-mannopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 102854-31-9 Methyl-2,6-di-O-benzyl-3,4-O-(1-ethoxyethyliden)-β-D-galactopyranosid 

Downstream Products

• 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 
• 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 

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

An exo-β-(1→3)-d-galactanase from Streptomyces sp. provides insights into type II arabinogalactan structure

An exo-β-(1→3)-d-galactanase (SGalase1) that specifically cleaves the β-(1→3)-d-galactan backbone of arabinogalactan-proteins (AGPs) was isolated from culture filtrates of a soil Streptomyces sp. Internal peptide sequence information was used to clone and recombinantly express the gene in E. coli. The molecular mass of the isolated enzyme was ～45 kDa, similar to the 48.2 kDa mass predicted from the amino acid sequence. The pI, pH and temperature optima for the enzyme were ～7.45, 3.8 and 48 °C, respectively. The native and recombinant enzymes specifically hydrolysed β-(1→3)-d- galacto-oligo- or poly-saccharides from the upstream (non-reducing) end, typical of an exo-acting enzyme. A second homologous Streptomyces gene (SGalase2) was also cloned and expressed. SGalase2 was similar in size (47.9 kDa) and enzyme activity to SGalase1 but differed in its pH optimum (pH 5). Both SGalase1 and SGalase2 are predicted to belong to the CAZy glycosyl hydrolase family GH 43 based on activity, sequence homology and phylogenetic analysis. The K m and Vmax of the native exo-β-(1→3)-d- galactanase for de-arabinosylated gum arabic (dGA) were 19 mg/ml and 9.7 μmol d-Gal/min/mg protein, respectively. The activity of these enzymes is well suited for the study of type II galactan structures and provides an important tool for the investigation of the biological role of AGPs in plants. De-arabinosylated gum arabic (dGA) was used as a model to investigate the use of these enzymes in defining type II galactan structure. Exhaustive hydrolysis of dGA resulted in a limited number of oligosaccharide products with a trisaccharide of Gal2GlcA1 predominating.

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.