50515-47-4

Basic information

• Product Name: N-tert-butoxycarbonyl-L-alanyl-D-glutaminyl-(α-benzyl)-γ-N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester
• Synonyms: N-tert-butoxycarbonyl-L-alanyl-D-glutaminyl-(α-benzyl)-γ-N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester
• CAS NO: 50515-47-4
• Molecular Weight: 903.042
• Mol File: 50515-47-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-tert-butoxycarbonyl-L-alanyl-D-glutaminyl-(α-benzyl)-γ-N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-butoxycarbonyl-L-alanyl-D-glutaminyl-(α-benzyl)-γ-N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester(50515-47-4)
• EPA Substance Registry System: N-tert-butoxycarbonyl-L-alanyl-D-glutaminyl-(α-benzyl)-γ-N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester(50515-47-4)

Safety Data

• Hazardous Substances Data: 50515-47-4(Hazardous Substances Data)

Upstream product

• 18814-54-5 N-ε-benzyloxycarbonyl-N-α-tert-butoxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester 
• 79338-14-0 D-glutamic acid 1-benzyl ester 
• 50515-48-5 (R)-5-(benzyloxy)-4-{(S)-2-[(tert-butoxycarbonyl)amino]propanamido}-5-oxopentanoic acid 
• 2389-45-9 Boc-Lys(Z)-OH 
• 2483-49-0 tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester 
• 678159-24-5 N-tert-butoxycarbonyl-L-alanyl-D-glutamic acid α-benzyl-γ-p-nitrophenyl ester 
• 47794-30-9 N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester trifluoroacetic acid salt 

Downstream Products

• 1203472-11-0 Boc-NH-L-Ala-γ-D-Glu(OMe)-L-Lys-(NHCbz)-D-Ala-D-Ala-OMe 

Relevant articles and documents

Synthesis of a Fragment of Bacterial Cell Wall

Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.