B5019
Benzyl 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside
Synonym(s):
β-D-Gal-(1→3)-α-D-GalNAc-1→OCH2Ph
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About This Item
Empirical Formula (Hill Notation):
C21H31NO11
CAS Number:
Molecular Weight:
473.47
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352201
MDL number:
InChI
1S/C21H31NO11/c1-10(25)22-14-19(33-21-18(29)17(28)15(26)12(7-23)32-21)16(27)13(8-24)31-20(14)30-9-11-5-3-2-4-6-11/h2-6,12-21,23-24,26-29H,7-9H2,1H3,(H,22,25)
SMILES string
CC(=O)NC1C(OCc2ccccc2)OC(CO)C(O)C1OC3OC(CO)C(O)C(O)C3O
InChI key
MYDRTQFLXCNCAG-UHFFFAOYSA-N
assay
≥97% (TLC)
form
powder
storage temp.
−20°C
Application
Benzyl 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside, a benzyl derivative of 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside, may be used in structural studies on the Lewis lec antigen.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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H Paulsen et al.
Carbohydrate research, 104(2), 195-219 (1982-06-16)
The hapten of the T-antigen was synthesized with a peptide-like amide-spacer as 2-(4-methoxycarbonylbutanecarboxamido)ethyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside and coupled with serum albumin to give a synthetic antigen. Other O-beta-D-galactopyranosyl haptens, 2-(4-methoxycarbonylbutanecarboxamido)ethyl 2-acetamido-2-deoxy-4-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside, O-beta-D-galactopyranosyl-(1 leads to 3)-O-[beta-D-galactopyranosyl-(1 leads to 4)]-2-acetamido-2-deoxy-alpha-D-galactopyranoside, and 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-glucopyranoside, the last
I Brockhausen et al.
Biochemistry, 24(8), 1866-1874 (1985-04-09)
Pig and rat colon mucosal membrane preparations catalyze the in vitro transfer of N-acetyl-D-glucosamine (GlcNAc) from UDP-GlcNAc to GalNAc-ovine submaxillary mucin to form GlcNAc beta 1-3GalNAc-mucin. Rat colon also catalyzes the in vitro transfer of GlcNAc from UDP-GlcNAc to GlcNAc
Phenyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside, a substrate for sialyltransferase.
W D Klohs et al.
Carbohydrate research, 89(2), 350-354 (1981-03-02)
Synthesis of 1-deoxynojirimycin-containing glycans related to the Lewis X and sialyl-Lewis X epitopes recognized by LEC-CAMs.
H Furui et al.
Carbohydrate research, 229(1), C1-C4 (1992-05-14)
P Reboul et al.
Glycoconjugate journal, 13(1), 69-79 (1996-02-01)
When treated with retinoic acid in vivo, C6 glioma cells show an enhancement of CMP-Neu5Ac:Gal beta 1-3 GalNAc-R alpha-2,3 sialyltransferase activity. A 300 kDa glycoprotein was detected by lectin affinoblotting in retinoic acid-treated C6 cells which stained weakly or not
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