387881-19-8

Basic information

• Product Name: 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester
• Synonyms: 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester
• CAS NO: 387881-19-8
• Molecular Weight: 1096.16
• Mol File: 387881-19-8.mol

Chemical Properties

• CAS DataBase Reference: 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester(387881-19-8)
• EPA Substance Registry System: 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester(387881-19-8)

Safety Data

• Hazardous Substances Data: 387881-19-8(Hazardous Substances Data)

Upstream product

• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 
• 387881-24-5 (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester 
• 387881-18-7 2-(2-{2-acetoxymethyl-5-acetylamino-6-benzyloxy-3-[4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-4-yloxy}-propionylamino)-propionic acid 2-trimethylsilanyl-ethyl ester 
• 387881-23-4 (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester 
• 387881-21-2 (S)-2-(trimethylsilyl)ethyl 2-((R)-2-(((2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanoate 
• 387881-17-6 (S)-2-[(R)-2-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-hydroxy-tetrahydro-pyran-4-yloxy)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester 
• 387881-22-3 (S)-2-[(R)-2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester 
• 73089-68-6 benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside 
• 103225-23-6 (S)-Alanin-(2-trimethylsilylethyl)ester 
• 70831-94-6 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide 

Downstream Products

• 367276-30-0 (S)-2-{(R)-2-[(2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 

Relevant articles and documents

Effect of the lipid II sugar moiety on bacterial transglycosylase: the 4-hydroxy epimer of lipid II is a TGase inhibitor

Lipid II analogues bearing major modifications on the second sugar (GlcNAc) were synthesized and evaluated for their substrate activity toward TGases. Unexpectedly, N-deacetyled lipid II decreased its activity dramatically, and the C4-axial OH lipid II became an inhibitor (IC50 = 8 μM) with an approximately 14-fold increase in binding affinity toward TGase (25 vs. 27).

Synthesis and evaluation of a new fluorescent transglycosylase substrate: Lipid II-based molecule possessing a dansyl-C20 polyprenyl moiety

(Figure Presented) The preparation of a novel fluorescent lipid II-based substrate for transglycosylases (TGases) is described. This substrate has characteristic structural features including a shorter lipid chain, a fluorophore tag at the end of the lipid chain rather than on the peptide chain, and no labeling with a radioactive atom. This fluorescent substrate is readily utilized In TGase activity assays to characterize TGases and also to evaluate the activities of TGase inhibitors.

Lipid II: Total synthesis of the bacterial cell wall precursor and utilization as a substrate for glycosyltransfer and transpeptidation by penicillin binding protein (PBP) 1b of Eschericia coli

An essential feature in the life cycle of both gram positive and gram negative bacteria is the production of new cell wall. Also known as murein, the cell wall is a two-dimensional polymer, consisting of a linear, repeating N-acetylmuramic acid (MurNAc) a