100929-00-8

Basic information

• Product Name: benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate
• Synonyms: benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate
• CAS NO: 100929-00-8
• Molecular Weight: 730.728
• Mol File: 100929-00-8.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate(100929-00-8)
• EPA Substance Registry System: benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate(100929-00-8)

Safety Data

• Hazardous Substances Data: 100929-00-8(Hazardous Substances Data)

Upstream product

• 67817-37-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 
• 118358-66-0 N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester 
• 67673-39-6 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 218291-40-8 (S)-3-((2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 68733-27-7 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl iodide 
• 167939-15-3 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate 
• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 68733-26-6 2-deoxy-2-azidogalactopyranose 
• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 
• 196398-25-1 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α/β-D-galactopyranosyl nitrate 
• 197158-78-4 1,2,3,4,6-penta-O-acetyl-D-galactopyranose 
• 67817-41-8 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride 

Downstream Products

• 100929-06-4 (S)-2-Amino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester 
• 218291-44-2 C₅₆H₆₆N₄O₂₃ 
• 100929-15-5 N,O-diacetyl-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galctopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzylester 
• 129415-19-6 C₄₅H₆₃N₅O₂₃ 
• 129415-18-5 O-allyl-N-<2-(4-pyridyl)ethoxycarbonyl>-L-tyrosyl-L-isoleucyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 
• 129432-10-6 N-<2-(4-pyridyl)ethoxycarbonyl>-L-threonyl-L-isoleucyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 
• 100929-13-3 N-<2-(4-pyridyl)ethoxycarbonyl>-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 100929-09-7 N-<2-(4-pyridyl)ethoxycarbonyl>-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 
• 120173-57-1 N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine 
• 100929-03-1 benzyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate 

Relevant articles and documents

Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides

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α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(αGalNAc)Ser] 3 and cyclo[Asp-(αGalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids αGalNAc-Ser 7 or αGalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by α-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with αGalN3Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 μM), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%).