182925-07-1

Basic information

• Product Name: N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->3)-L-serine benzyl ester
• Synonyms: N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->3)-L-serine benzyl ester
• CAS NO: 182925-07-1
• Molecular Weight: 1164.09
• Mol File: 182925-07-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->3)-L-serine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->3)-L-serine benzyl ester(182925-07-1)
• EPA Substance Registry System: N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2,3-di-O-acetyl-β-D-xylopyranosyl)-(1->3)-L-serine benzyl ester(182925-07-1)

Safety Data

• Hazardous Substances Data: 182925-07-1(Hazardous Substances Data)

Upstream product

• 21209-51-8 N-benzyloxycarbonyl-L-serine benzyl ester 
• 1010795-04-6 C₃₇H₄₈Cl₃NO₂₄ 
• 182925-06-0 Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-4,5-diacetoxy-6-hydroxy-tetrahydro-pyran-3-yloxy)-4-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 359689-81-9 p-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside 
• 249928-97-0 Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-[(3R,4S,5R,6S)-4,5-diacetoxy-6-(3-nitro-pyridin-2-yloxy)-tetrahydro-pyran-3-yloxy]-4-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

3-Nitro-2-pyridyl glycoside as donor for chemical glycosylation and its application to chemoenzymatic synthesis of oligosaccharide

3-Nitro-2-pyridyl (3NPy) glycosides, which act as versatile glycosyl donors in enzymatic transglycosylation, can also be chemically activated. Chemical glycosylation with protected 3NPy glycosides was readily effected at -20°C by using TMSOTf as a catalyst to afford the desired glycosides in good yields. A trisaccharide serine conjugate Gal(β1-3)Gal(β1-4)Xylβ-Ser was synthesized by combined use of enzymatic and chemical glycosylations. The trisaccharide 3NPy glycoside was prepared by stepwise transglycosylation of a Gal-3NPy donor to a Xyl-3NPy acceptor by using a β-galactosidase. After protection of the free hydroxy groups of the trisaccharide by acetylation, the 3NPy glycoside was then subjected to chemical glycosylation of a serine residue to afford the trisaccharide serine conjugate.

Chemoenzymatic synthesis of Gal(β1-3)Gal(β1-4)Xyl(β)-L-Ser and Gal(β1-3)Gal(β1-4)Xyl(β)-MU by the use of β-D-galactosidase

The title trisaccharide-serine conjugate 1 constituting the linkage region between glycosaminoglycan and protein in proteoglycan, was synthesized via a trisaccharide p-nitrophenyl (PNP) glycoside prepared by stepwise enzymatic transglycosidation to Xyl-PNP with a β-D-galactosidase. In the second transglycosidation step, partial protection of the disaccharide intermediate, Gal-Xyl-PNP, furnished selective galactosylation at the 3'-position. Cleavage of the PNP group after peracetylation, chemical coupling with serine and final deprotection afforded 1. Fluorescence labeled trisaccharide, Gal(β1-3)Gal(β1-4)Xyl(β)-MU (MU: 4-methylumbelliferyl) (2) was also synthesized in a simalar way.