119645-65-7

Basic information

• Product Name: Z-ALA-TRP-OH
• Synonyms: Cbz-Ala-Trp-OH;Z-L-alanyl-L-tryptophan≥ 98% (HPLC);Z-L-ALANYL-L-TRYPTOPHAN;Z-ALA-TRP-OH
• CAS NO: 119645-65-7
• Molecular Formula: C₂₂H₂₃N₃O₅
• Molecular Weight: 409.44
• Mol File: 119645-65-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 742.3°C at 760 mmHg
• Flash Point: 402.7°C
• Appearance: /
• Density: 1.329g/cm³
• Vapor Pressure: 3.88E-23mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-ALA-TRP-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ALA-TRP-OH(119645-65-7)
• EPA Substance Registry System: Z-ALA-TRP-OH(119645-65-7)

Safety Data

• Hazardous Substances Data: 119645-65-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C22H23N3O5/c1-14(24-22(29)30-13-15-7-3-2-4-8-15)20(26)25-19(21(27)28)11-16-12-23-18-10-6-5-9-17(16)18/h2-10,12,14,19,23H,11,13H2,1H3,(H,24,29)(H,25,26)(H,27,28)

Upstream product

• 28944-98-1 Z-L-Ala-L-Trp-OMe 
• 1142-20-7 N-Cbz-Ala 
• 73-22-3 L-Tryptophan 
• 820239-42-7 benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate 

Downstream Products

• 128228-48-8 {(S)-1-[4-(1H-Indol-3-ylmethyl)-5-oxo-4,5-dihydro-oxazol-2-yl]-ethyl}-carbamic acid benzyl ester 
• 128228-48-8 {(S)-1-[(S)-4-(1H-Indol-3-ylmethyl)-5-oxo-4,5-dihydro-oxazol-2-yl]-ethyl}-carbamic acid benzyl ester 
• 1621538-56-4 N^α-{[(benzyloxy)carbonyl]-L-alanyl}-1-{[(benzyloxy)carbonyl]-L-phenylalanyl}-L-tryptophan 
• 928787-82-0 Cbz-L-Ala-L-Trp-Bt 
• 119645-71-5 1-((S)-1-Benzyloxycarbonylamino-ethyl)-4,9-dihydro-3H-β-carboline-3-carboxylic acid 

Relevant articles and documents

A new class of α-ketoamide derivatives with potent anticancer and anti-SARS-CoV-2 activities

Inhibitors of the proteasome have been extensively studied for their applications in the treatment of human diseases such as hematologic malignancies, autoimmune disorders, and viral infections. Many of the proteasome inhibitors reported in the literature target the non-primed site of proteasome's substrate binding pocket. In this study, we designed, synthesized and characterized a series of novel α-keto phenylamide derivatives aimed at both the primed and non-primed sites of the proteasome. In these derivatives, different substituted phenyl groups at the head group targeting the primed site were incorporated in order to investigate their structure-activity relationship and optimize the potency of α-keto phenylamides. In addition, the biological effects of modifications at the cap moiety, P1, P2 and P3 side chain positions were explored. Many derivatives displayed highly potent biological activities in proteasome inhibition and anticancer activity against a panel of six cancer cell lines, which were further rationalized by molecular modeling analyses. Furthermore, a representative α-ketoamide derivative was tested and found to be active in inhibiting the cellular infection of SARS-CoV-2 which causes the COVID-19 pandemic. These results demonstrate that this new class of α-ketoamide derivatives are potent anticancer agents and provide experimental evidence of the anti-SARS-CoV-2 effect by one of them, thus suggesting a possible new lead to develop antiviral therapeutics for COVID-19.

Convenient synthesis of C-terminal di- and tri-peptide amides from N-protected dipeptidoylbenzotriazoles

N-Protected dipeptidoylbenzotriazoles react with aqueous ammonia to give dipeptide primary amides (77-98%) and with N-unprotected α-amino amides to afford tripeptide primary amides (82-86%).

Highly diastereoselective peptide chain extensions of unprotected amino acids with N-(Z-α-aminoacyl)benzotriazoles

Coupling an unprotected amino acid or dipeptide in partially aqueous solution with a readily available N-(Z-α-amino-acyl)benzotriazole or N-(Z-α-aminopetidoyl)benzotriazole affords N-terminal-protected di-, tri-, and tetrapeptides in yields of 85-98% (average 95% for 2a-i, 93% for 4a-f and 4a′, 86% for 5a-b) with minimal epimerization.