1421-69-8

Basic information

• Product Name: Z-GLY-LEU-OH
• Synonyms: N-BENZYLOXYCARBONYLGLYCYL-L-LEUCINE;Z-GLYCYL-L-LEUCINE;Z-GLY-LEU;Z-GLY-LEU-OH;Z-L-GLYCYL-L-LEUCINE;BENZYLOXYCARBONYLGLYCYL-L-LEUCINE;N-cbz-gly-leu;N-[N-[(phenylmethoxy)carbonyl]glycyl]-L-leucine
• CAS NO: 1421-69-8
• Molecular Formula: C₁₆H₂₂N₂O₅
• Molecular Weight: 322.36
• EINECS: 215-825-3
• Product Categories: Amino Acid Derivatives
• Mol File: 1421-69-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 99-100 °C
• Boiling Point: 582 °C at 760 mmHg
• Flash Point: 305.8 °C
• Appearance: /
• Density: 1.203 g/cm³
• Vapor Pressure: 2.17E-14mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: −20°C
• CAS DataBase Reference: Z-GLY-LEU-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLY-LEU-OH(1421-69-8)
• EPA Substance Registry System: Z-GLY-LEU-OH(1421-69-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1421-69-8(Hazardous Substances Data)

Usage

General Description

Z-GLY-LEU-OH, also known as N-(tert-butoxycarbonyl)-glycyl-leucine, is a chemical compound consisting of the amino acids glycine and leucine connected by a peptide bond. Z-GLY-LEU-OH is commonly used in biochemical and pharmaceutical research due to its ability to mimic the structure and function of naturally occurring peptides. Z-GLY-LEU-OH is typically used as a substrate to study the activity of enzymes such as proteases and peptidases, as well as to study the mechanisms of peptide bond cleavage and protein degradation. It is also a key component in the synthesis of various peptide-based drugs and pharmaceuticals, highlighting its importance in the field of medicinal chemistry. Overall, Z-GLY-LEU-OH plays a crucial role in advancing our understanding of protein structure and function, as well as in the development of new therapeutics for a variety of human diseases.

InChI:InChI=1/C16H22N2O5/c1-11(2)8-13(15(20)21)18-14(19)9-17-16(22)23-10-12-6-4-3-5-7-12/h3-7,11,13H,8-10H2,1-2H3,(H,17,22)(H,18,19)(H,20,21)/t13-/m1/s1

Upstream product

• 17331-93-0 N-benzyloxycarbonylglycyl-L-leucine methyl ester 
• 61-90-5 L-leucine 
• 2899-57-2 Sphenyl N-benzyloxycarbonylaminoethanothioate 
• 7364-46-7 N-trimethylsilanyl-L-leucine trimethylsilanyl ester 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 2743-40-0 L-leucine ethyl ester hydrochloride 
• 6687-17-8 2-(N-benzyloxycarbonyl-glycyl)-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one 
• 7535-72-0 (N-carboxybenzylglycinyl)leucinamide 
• 67-56-1 methanol 
• 173459-80-8 benzyl [2?(1H?benzo[d][1,2,3]triazol?1?yl)?2?oxoethyl]carbamate 
• 1280225-75-3 C₂₀H₂₄N₂O₆ 
• 2899-56-1 N-benzyloxycarbonylglycine cyanomethylester 
• 1738-86-9 Z-Gly-ONp 
• 869-19-2 Glycyl-L-leucine 

Downstream Products

• 16816-39-0 N-[N-(N-benzyloxycarbonyl-glycyl)-L-leucyl]-glycine methyl ester 
• 17331-93-0 N-benzyloxycarbonylglycyl-L-leucine methyl ester 
• 16295-38-8 Cbz-Gly-L-Leu-Gly 
• 103818-53-7 N-carbobenzoxyglycyl-L-leucylcyanamide 
• 1005496-75-2 (1-{[2-(3-imino-4-oxo-4-phenylbutyrylamino)-4-methylpentanoylamino]methyl}vinyl)phosphonic acid dibenzyl ester 
• 1356488-84-0 Cbz-glycyl-(L)-leucyl benzotriazole 
• 1380332-75-1 cyclo(Z-Gly-Leu) 

Relevant articles and documents

Affinity chromatography of alkaline proteinase S on N-carbobenzoxyglycylleucylaminohexyl-Sepharose.

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A new benzotriazole-mediated stereoflexible gateway to hetero-2,5- diketopiperazines

Open chain Cbz-L-aa1-L-Pro-Bt (Bt=benzotriazole) sequences were converted into either the corresponding trans- or cis-fused 2,5- diketopiperazines (DKPs) depending on the reaction conditions. Thermodynamic tandem cyclization/epimerization afforded selectively the corresponding trans-DKPs (69-75%). Complementarily, tandem deprotection/cyclization led to the cis-DKPs (65-72%). A representative set of proline-containing cis- and trans-DKPs has been prepared. A mechanistic investigation, based on chiral HPLC, kinetics, and computational studies enabled a rationalization of the results. Stereoflexible route to DKPs: A convenient, versatile, and flexible benzotriazole-mediated methodology for the synthesis of proline-containing hetero-2,5-diketopiperazines (DKPs) is reported. Depending on the reaction conditions, either cis- or trans-configured DKPs were obtained starting from the same inexpensive l,l-dipeptidoyl benzotriazole key intermediate (see scheme). Kinetics, chiral HPLC, and computational studies forged a background for mechanistic rationalization. Copyright

Peptide coupling of unprotected amino acids through in situ p-nitrophenyl ester formation

Several series of dipeptides and tripeptides were prepared via an activation-coupling method involving the in situ formation of a p-nitrophenyl ester of an (N-protected) amino acid, followed by coupling with an unprotected amino acid in partially aqueous solutions. The resulting peptide is easily isolated by precipitation. In general, the yields obtained are good to excellent and racemization is minimal. This method is particularly advantageous with respect to its simplicity and lack of obligatory side chain protection/deprotection steps.