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3-O-[2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL]-D-MANNOPYRANOSE - CAS 210036-24-1

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Category
Main Product
Product Name
3-O-[2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL]-D-MANNOPYRANOSE
Catalog Number
210036-24-1
Synonyms
GlcNAcβ1-3Man;
CAS Number
210036-24-1
Molecular Weight
0
Molecular Formula
C14H25NO11
COA
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MSDS
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Canonical SMILES
CC(=O)NC1C(C(C(OC1OC2C(C(OC(C2O)O)CO)O)CO)O)O
InChI
InChI=1S/C14H25NO11/c1-4(18)15-7-10(21)8(19)5(2-16)25-14(7)26-12-9(20)6(3-17)24-13(23)11(12)22/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8-,9-,10-,11+,12+,13?,14+/m1/s1
InChIKey
IXWNIYCPCRHGAE-DLDFRZNISA-N
Structure
CAS 210036-24-1 3-O-[2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL]-D-MANNOPYRANOSE
Specification
Purity
95%
Boiling Point
795.471ºC at 760 mmHg
Density
1.645g/cm3
Appearance
Off-White Crystalline Powder
Reference Reading
1.Synthesis and molecular modelling of unsaturated exomethylene pyranonucleoside analogues with antitumor and antiviral activities.
Agelis G1, Tzioumaki N, Tselios T, Botić T, Cencic A, Komiotis D. Eur J Med Chem. 2008 Jul;43(7):1366-75. Epub 2007 Oct 18.
This report describes the total and facile synthesis of the unsaturated keto and exomethylene pyranonucleoside analogues, 1-(2,3,4-trideoxy-4-methylene-6-O-trityl-alpha-D-glycero-hex-2-enopyranosyl)uracil (10), 1-(2,3-dideoxy-alpha-D-glycero-hex-2-enopyranosyl-4-ulose)uracil (17) and 1-(2,3,4-trideoxy-4-methylene-alpha-D-glycero-hex-2-enopyranosyl)uracil (18). Commercially available 1,2,3,4,6-penta-O-acetyl-alpha-D-mannopyranose (1) was condensed with silylated uracil, deacetylated and acetalated to afford 1-(2,3-O-isopropylidene-alpha-D-mannopyranosyl)uracil (4). Two different synthetic routes were investigated for the conversion of 4 into the olefinic derivative 1-(2,3,4-trideoxy-4-methylene-6-O-trityl-alpha-D-glycero-hex-2-enopyranosyl)uracil (10). Although the two procedures are quite similar with respect to yields and final products, the second also leads to the keto-2',3'-unsaturated analogue (17). The new analogues were evaluated for their anticancer and antiviral activities using several tumor cell lines and gastrointestinal rotavirus.
2.Stereoselective (2-naphthyl)methylation of sugar hydroxyls by the hydrogenolysis of diastereoisomeric dioxolane-type (2-naphthyl)methylene acetals.
Borbás A1, Szabó ZB, Szilágyi L, Bényei A, Lipták A. Carbohydr Res. 2002 Nov 19;337(21-23):1941-51.
The cis axial/equatorial OH groups of methyl alpha-L- and ethyl 1-thio-alpha-L-rhamnopyranoside, 1,6-anhydro-beta-D-mannopyranose, and 1,6-anhydro-beta-D-galactopyranose were reacted with 2-naphthaldehyde dimethyl acetal to diastereomeric dioxolane-type 2,3-O-(2-naphthyl)methylene or 3,4-O-(2-naphthyl)methylene acetals. The glycosides yielded the exo- and endo-isomers in nearly 1:1 ratio, 1,6-anhydro-beta-D-mannopyranose gave predominantly the endo-, and 1,6-anhydro-beta-D-galactopyranose exclusively endo-isomer. The acetals and some of their fully protected derivatives bearing benzyl or tert-butyldimethylsilyl groups were hydrogenolised with AlH(3) (3LiAlH(4)-AlCl(3)) or with Me(3)N.BH(3)-AlCl(3) reagents. The endo-isomers were cleaved by both reagents to give axial NAP ethers, the exo-isomers of pyranosides furnished equatorial NAP ethers. However, the exo-isomers of pyranoses gave irregular axial ethers with a > 30-fold enhancement of the reaction rates with respect to the endo-isomer.
3.Preparation of branched cyclomaltoheptaose with 3-O-α-L-fucopyranosyl-α-D-mannopyranose and changes in fucosylation of HCT116 cells treated with the fucose-modified cyclomaltoheptaose.
Kimura M1, Masui Y, Shirai Y, Honda C, Moriwaki K, Imai T, Takagi U, Kiryu T, Kiso T, Murakami H, Nakano H, Kitahata S, Miyoshi E, Tanimoto T. Carbohydr Res. 2013 Jun 7;374:49-58. doi: 10.1016/j.carres.2013.03.022. Epub 2013 Apr 3.
From a mixture of 4-nitrophenyl α-L-fucopyranoside and D-mannopyranose, 3-O-α-L-fucopyranosyl-D-mannopyranose was synthesised through the transferring action of α-fucosidase (Sumizyme PHY). 6(I),6(IV)-Di-O-(3-O-α-L-fucopyranosyl-α-D-mannopyranosyl)-cyclomaltoheptaose {8, 6(I),6(IV)-di-O-[α-L-Fuc-(1→3)-α-D-Man]-βCD} was chemically synthesised using the trichloroacetimidate method. The structures were confirmed by MS and NMR spectroscopy. A cell-based assay using the fucosyl βCD derivatives, including the newly synthesised 8, showed that derivatives with two branches of the α-L-Fuc or α-L-Fuc-(1→3)-α-D-Man residues possessed slight growth-promoting effects and lower toxicity in HCT116 cells compared to those with one branch. These compounds may be useful as drug carriers in targeted drug delivery systems.
4.Isolation and identification of poly-alpha-(1-->4)-linked 3-O-methyl-D-mannopyranose from a hot-water extract of Mycobacterium vaccae.
Tian XX1, Li A, Farrugia IV, Mo X, Crich D, Groves MJ. Carbohydr Res. 2000 Jan 29;324(1):38-44.
A polysaccharide around 3.6 kDa has been identified as the major carbohydrate moiety of a antineoplastic protein-polysaccharide complex (PS4A) obtained by boiling intact cells of Mycobacterium vaccae in water. 1H and 13C NMR spectra of this polysaccharide suggested it was a highly homogeneous polymer composed substantially of one monomer, probably an alpha-linked O-methylated mannose. Comparison of the COSY spectra of the original and acetylated polymer indicated that the glycosidic linkage and the methyl ether were interchangeable, at O-3 and O-4. Further study demonstrated that the benzyolated hydrolysate of the polymer was 1,2,4,6-tetra-O-benzoyl-3-O-methyl-beta-mannopyranose. The hydrolysate was 3-O-methyl-alpha, beta-mannopyranose and the polymer was therefore poly-alpha-(1-->4)-linked 3-O-methyl-D-mannopyranose. This conclusion was further confirmed with an authentic sample of the monomer, which had spectral data identical to those of the hydrolyzate and co-eluted from an ion-exchange HPLC with the major sugar in the hydrolysate.
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