1380302-95-3

Basic information

• Product Name: N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl)-L-threonine benzylester
• CAS NO: 1380302-95-3
• Molecular Weight: 760.795
• Mol File: 1380302-95-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl)-L-threonine benzylester(CAS DataBase Reference)
• NIST Chemistry Reference: N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl)-L-threonine benzylester(1380302-95-3)
• EPA Substance Registry System: N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl)-L-threonine benzylester(1380302-95-3)

Safety Data

• Hazardous Substances Data: 1380302-95-3(Hazardous Substances Data)

Upstream product

• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 151909-93-2 1,3,4,6-Tetra-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-α/β-D-galactopyranose 
• 195142-26-8 1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate 
• 1380302-92-0 N^α-fluoren-9-ylmethoxycarbonyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxy-carbonylamino)-β-Dgalactopyranosyl]-L-threonine benzyl ester 
• 108-24-7 acetic anhydride 
• 73724-48-8 N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester 
• 73731-37-0 Fmoc-Thr-OH 
• 100-39-0 benzyl bromide 
• 10385-50-9 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-galactopyranoside 
• 41355-44-6 2-acetamido-2,4,6,-tri-O-acetyl-1-chloro-1,2-dideoxy-α-D-galactopyranose 

Relevant articles and documents

A Synthetic MUC1 Glycopeptide Bearing βGalNAc-Thr as a Tn Antigen Isomer Induces the Production of Antibodies against Tumor Cells

This study presents the synthesis of the novel protected O-glycosylated amino acid derivatives 1 and 2, containing βGalNAc-SerOBn and βGalNAc-ThrOBn units, respectively, as mimetics of the natural Tn antigen (αGalNAc-Ser/Thr), along with the solid-phase assembly of the glycopeptides NHAcSer-Ala-Pro-Asp-Thr[αGalNAc]-Arg-Pro-Ala-Pro-Gly-BSA (3-BSA) and NHAcSer-Ala-Pro-Asp-Thr[βGalNAc]-Arg-Pro-Ala-Pro-Gly-BSA (4-BSA), bearing αGalNAc-Thr or βGalNAc-Thr units, respectively, as mimetics of MUC1 tumor mucin glycoproteins. According to ELISA tests, immunizations of mice with βGalNAc-glycopeptide 4-BSA induced higher sera titers (1:320 000) than immunizations with αGalNAc-glycopeptide 3-BSA (1:40 000). Likewise, flow cytometry assays showed higher capacity of the obtained anti-glycopeptide 4-BSA antibodies to recognize MCF-7 tumor cells. Cross-recognition between immunopurified anti-βGalNAc antibodies and αGalNAc-glycopeptide and vice versa was also verified. Lastly, molecular dynamics simulations and surface plasmon resonance (SPR) showed that βGalNAc-glycopeptide 4 can interact with a model antitumor monoclonal antibody (SM3). Taken together, these data highlight the improved immunogenicity of the unnatural glycopeptide 4-BSA, bearing βGalNAc-Thr as Tn antigen isomer.