384346-85-4

Basic information

• Product Name: N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester
• Synonyms: N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester;N-FMoc-O-[2-acetaMido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine Allyl Ester;N-Fmoc-4,6-benzylidene-2’’’’tetra-O-acetyl T Epitope, Threonyl Allyl Ester;O-[2-Acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-b-D-galactopyranosyl)-a-D-galactopyranosyl]-N-Fmoc-L-threonine allyl ester
• CAS NO: 384346-85-4
• Molecular Formula: C₅₁H₅₈N₂O₁₉
• Molecular Weight: 1003.00822
• Product Categories: Amino Acids & Derivatives;Aromatics;Chiral Reagents;Oligosaccharides;Amino Acids & Derivatives, Aromatics, Chiral Reagents, Oligosaccharides
• Mol File: 384346-85-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane
• CAS DataBase Reference: N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester(384346-85-4)
• EPA Substance Registry System: N-Fmoc-4,6-benzylidene-2’3’4’6’-tetra-O-acetyl T Epitope, Threonyl Allyl Ester(384346-85-4)

Safety Data

• Hazardous Substances Data: 384346-85-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 507-09-5 tiolacetic acid 
• 384346-84-3 N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine allyl ester 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 384346-81-0 N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 
• 384346-80-9 4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside 
• 273944-57-3 N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 
• 125760-23-8 4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 125760-22-7 p-methylphenyl 2-deoxy-2-azido-1-thio-β-D-galactopyranoside 
• 136523-92-7 N-(9-fluorenylmethoxycarbonyl)-L-threonine allyl ester 
• 73731-37-0 Fmoc-Thr-OH 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 

Downstream Products

• 174783-86-9 N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine 

Relevant articles and documents

Chemoenzymatic synthesis of sialylated glycopeptides derived from mucins and T-cell stimulating peptides

The Tn, T, sialyl-Tn, and 2,3-sialyl-T antigens are tumor-associated carbohydrate antigens expressed on mucins in epithelial cancers, such as those affecting the breast, ovary, stomach, and colon. Glycopeptides carrying these antigens are of interestfor development of cancer vaccines and a short, chemoenzymatic strategy for their synthesis is reported. Building blocks corresponding to the Tn (Ga1NAcα-Ser/Thr) and T [Galβ(1→3)Ga1NAcα-Ser/Thr] antigens, which are relatively easy to obtain by chemical synthesis, were prepared and then used in the synthesis of glycopeptides on the solid phase. Introduction of sialic acid to give the sialyl-Tn [Neu5Acα(2→6)Ga1NAcα-Ser/Thr] and 2,3-sialyl-T [Neu5Acα(2→3)Ga1β(1→3)Ga1NAcα-Ser/ Thr] antigens is difficult when performed chemically at the building block level. Sialylation was therefore carried out with recombinant sialyltransferases in solution after cleavage of the Tn and T glycopeptides from the solid phase. In the same manner, the core 2 trisaccharide [Ga1β1→3(G1cNAcβ1→6)Ga1NAc] was incorporated in glycopeptides containing the T antigen by using a recombinant N-acetylglucosaminyltransferase. The outlined chemoenzymatic approach was applied to glycopeptides from the tandem repeat domain of the mucin MUCl, as well as to neoglycosylated derivatives of a T cell stimulating viral peptide.