24458-14-8

Basic information

• Product Name: H-Lys(Z)-OBzl
• Synonyms: N-ε-Z-L-lysine benzyl ester;L-Lysine, N6-[(phenylMethoxy)carbonyl]-, phenylMethyl ester;(S)-benzyl 2-aMino-6-(((benzyloxy)carbonyl)aMino)hexanoate
• CAS NO: 24458-14-8
• Molecular Formula: C₂₁H₂₆N₂O₄
• Molecular Weight: 370.446
• Mol File: 24458-14-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 536.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.163±0.06 g/cm3(Predicted)
• PKA: 12.67±0.46(Predicted)
• CAS DataBase Reference: H-Lys(Z)-OBzl(CAS DataBase Reference)
• NIST Chemistry Reference: H-Lys(Z)-OBzl(24458-14-8)
• EPA Substance Registry System: H-Lys(Z)-OBzl(24458-14-8)

Safety Data

• Hazardous Substances Data: 24458-14-8(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 2389-45-9 Boc-Lys(Z)-OH 
• 6366-70-7 N^ε-carbobenzoxy-L-lysine benzyl ester hydrochloride 
• 100-51-6 benzyl alcohol 
• 405-39-0 N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine 
• 77236-13-6 N-α-tert-Butyloxycarbonyl-N-ε-carbobenzoxy-L-lysine benzyl ester 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 

Downstream Products

• 72087-22-0 Boc-Asn-Lys(Z)-OBzl 
• 150151-63-6 N-ε-Carbobenzyloxy-N-α-(indole-3-acetyl)-L-lysine benzyl ester 
• 84716-96-1 N^ε-(Benzyloxycarbonyl)-N^α-(3-cyanopropanoyl)-L-lysine benzyl ester 
• 98317-55-6 Tert-butyloxycarbonyltyrosyl-glycyl-glycyl-phenylalanyl-leucyl-ε-benzyloxycarbonyllysine Benzyl Ester 
• 32769-96-3 Boc-Lys(Z)-Lys(Z)-OBzl 
• 128843-83-4 Benzyl 2,3-anhydro-α-L-lyxopyranoside 
• 96728-27-7 (S)-6-Benzyloxycarbonylamino-2-((1R,4R,5R,6S)-4-benzyloxy-5-hydroxy-3-oxa-7-aza-bicyclo[4.1.0]hept-7-yl)-hexanoic acid benzyl ester 
• 95066-26-5 (S)-6-Benzyloxycarbonylamino-2-((1R,2R,5S,6R)-2-benzyloxy-3,7-dioxa-bicyclo[4.1.0]hept-5-ylamino)-hexanoic acid benzyl ester 
• 95066-28-7 benzyl 2,3-anhydro-β-L-lyxopyranoside 
• 96728-25-5 (S)-6-Benzyloxycarbonylamino-2-((1S,4R,5S,6R)-4-benzyloxy-5-hydroxy-3-oxa-7-aza-bicyclo[4.1.0]hept-7-yl)-hexanoic acid benzyl ester 
• 95066-25-4 (S)-6-Benzyloxycarbonylamino-2-((1S,2R,5R,6S)-2-benzyloxy-3,7-dioxa-bicyclo[4.1.0]hept-5-ylamino)-hexanoic acid benzyl ester 
• 112952-81-5 Boc-Asn-Tyr-Lys(Z)-OBzl 
• 33838-60-7 BocD(OBzl)K(Z)OBzl 
• 82254-65-7 (S)-2-((S)-2-Amino-6-benzyloxycarbonylamino-hexanoylamino)-6-benzyloxycarbonylamino-hexanoic acid benzyl ester 

Relevant articles and documents

A conformationally constrained fused tricyclic nisin AB-ring system mimic toward an improved pyrophosphate binder of lipid II

The bacteria-specific membrane component lipid II is essential for bacterial cell wall synthesis. A tricyclic nisin mimic was designed and synthesized in which both thioether moieties were mimicked by an alkane-bridge, as well as the introduction of a third conformational constraint consisting of a macrocyclic lactam-bridge between the N-terminus and the B-ring. The newly designed tricyclic AB-ring mimic was found to bind lipid II since it was able to inhibit nisin-induced membrane leakage in a dose-dependent manner. These results imply that the tricyclic AB-ring mimic may form a novel class of lead structures for the development of nisin-based peptide antibiotics.

Solution-phase automated synthesis of tripeptide derivatives

An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, dichloromethane. As an application of the automated synthesis apparatus, 216 fragment tripeptide derivatives were synthesized systematically using the MSA method, in excellent yield and with increased efficiency.

Application of a unique automated synthesis system for solution-phase peptide synthesis

An automated synthesis system, which is suitable for repetitive syntheses using similar reaction procedures, was used to synthesize systematically a library of all possible dipeptides (25) and tripeptides (125) from 5 protected amino acids. The apparatus has also been applied to the automated synthesis of 10 fragment tripeptide derivatives that are constituents of the hormone PACAP-27. The measured molecular optical rotation values of the library of 125 tripeptides were found to correlate well with calculated values obtained by summation of the molecular optical rotation values for the constituent amino acids.