3397-35-1

Basic information

• Product Name: Z-LEU-OSU
• Synonyms: N-CBZ-L-LEUCINE N-HYDROXYSUCCINIMIDE ESTER;N-BENZYLOXYCARBONYL-L-LEUCINE N-HYDROXYSUCCINIMIDE ESTER;N-CARBOBENZOXY-L-LEUCINE-N-HYDROXYSUCCINIMIDE ESTER;Z-LEU-OSU;Z-LEUCINE-OSU;Z-L-LEUCINE HYDROXYSUCCINIMIDE ESTER;Z-L-LEUCINE-N-HYDROXYSUCCINIMIDE ESTER;BENZYLOXYCARBONYL-L-LEUCINE N-HYDROXYSUCCINIMIDE ESTER
• CAS NO: 3397-35-1
• Molecular Formula: C₁₈H₂₂N₂O₆
• Molecular Weight: 362.38
• EINECS: 222-256-4
• Product Categories: Z-Amino Acids and Derivatives
• Mol File: 3397-35-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 118-120 °C
• Appearance: Off-white to white/Solid
• Density: 1.28 g/cm³
• Refractive Index: 1.561
• Storage Temp.: −20°C
• PKA: 10.60±0.46(Predicted)
• CAS DataBase Reference: Z-LEU-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: Z-LEU-OSU(3397-35-1)
• EPA Substance Registry System: Z-LEU-OSU(3397-35-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 3397-35-1(Hazardous Substances Data)

Usage

Chemical Description

Z-Leu-OSu is a chemical used as a reagent for the synthesis of amides.

InChI:InChI=1/C18H22N2O6/c1-12(2)10-14(17(23)26-20-15(21)8-9-16(20)22)19-18(24)25-11-13-6-4-3-5-7-13/h3-7,12,14H,8-11H2,1-2H3,(H,19,24)

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 2018-66-8 Z-Leu-OH 

Downstream Products

• 102096-29-7 [(S)-1-(6-Methoxy-quinolin-8-ylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 52616-94-1 Z-Leu-Pro-OBu^t 
• 53481-48-4 (S)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoate 
• 448963-25-5 (S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-5-ureido-pentanoic acid 
• 289043-10-3 {(S)-1-[2-(4-Methoxy-phenylamino)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester 
• 71730-80-8 Z-L-Leu-D-Leu-OMe 
• 886758-80-1 [(S)-1-((S)-1-Carbamoyl-2-p-tolyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 886758-81-2 [(S)-1-((S)-1-Carbamoyl-2-m-tolyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 225122-46-3 3-benzyloxy-2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionic acid 
• 886758-89-0 (S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-3-(4-methoxy-phenyl)-propionic acid 
• 13512-34-0 (S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester 
• 886758-83-4 (S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-3-(4-trifluoromethyl-phenyl)-propionic acid methyl ester 
• 886758-82-3 {(S)-1-[(S)-2-(4-Benzyloxy-phenyl)-1-carbamoyl-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester 

Relevant articles and documents

Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands

The enantioselective alkylation of aldehydes catalysed by nickel(ii)-complexes derived from α-amino amides was studied by means of density functional theory (DFT) and ONIOM (B3LYP:UFF) calculations. A mechanism was proposed in order to investigate the origin of enantioselectivity. The chirality-determining step for the alkylation was the formation of the intermediate complexes with the involvement of a 5/4/4-fused tricyclic transition state. The predominant products predicted theoretically were of (S)-configuration, in good agreement with experimental observations. The scope of the reaction was examined and high yields and enantioselectivities were observed for the enantioselective addition of Et2Zn and Me2Zn to aromatic and aliphatic aldehydes.

Bispidine as a secondary structure nucleator in peptides

Here we describe bispidine as a scaffold for inducing open turn-like and beta sheet conformations on the attached peptides depending on the mode of attachment of peptides to the scaffold. Various bispidine-peptide conjugates were designed and synthesized to demonstrate the versatility of the scaffold.

FLUOROGENIC PEPTIDASE SUBSTRATE

The invention is related to new peptidase substrates of formula (I) : wherein - R1 is a peptidyl or amino acid moiety directly linked to W via its carbonyl function or one of its carbonyl functions, or, R1 is a chain R'1-NH-Y-C(O)- in which R'1 is a peptidyl or amino acid moiety directly linked to the NH of the R1 chain via its carbonyl function or one of its carbonyl functions and Y is an organic spacer, - W is O, NH or NR2 with R2 representing a (C1-C4)alkyl, - T and Rb are as defined in claim 1, and a process for detecting the presence of a catalytically active peptidase, using one of such substrates.