7669-64-9

Basic information

• Product Name: Z-PHE-PRO-OH
• Synonyms: N-CARBOBENZOXY-L-PHENYLALANYL-L-PROLINE;Z-PHE-PRO-OH;Z-L-PHENYLALANYL-L-PROLINE;CBZ-L-PHE-L-PRO;1-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-proline;Cbz-L-Phe-L-Pro-OH;N-(Benzyloxycarbonyl)-Phe-Pro-OH;Z-L-Phe-L-Pro-OH
• CAS NO: 7669-64-9
• Molecular Formula: C₂₂H₂₄N₂O₅
• Molecular Weight: 396.44
• EINECS: 231-645-8
• Mol File: 7669-64-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 107-108 °C
• Boiling Point: 669.586°C at 760 mmHg
• Flash Point: 358.753°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: -15°C
• PKA: 3.51±0.20(Predicted)
• CAS DataBase Reference: Z-PHE-PRO-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PHE-PRO-OH(7669-64-9)
• EPA Substance Registry System: Z-PHE-PRO-OH(7669-64-9)

Safety Data

• Hazardous Substances Data: 7669-64-9(Hazardous Substances Data)

Usage

General Description

Z-PHE-PRO-OH is a chemical compound that consists of three amino acids: phenylalanine, proline, and hydroxyproline. It is commonly used in biochemistry and pharmaceutical research as a model peptide for studying the behavior and interactions of proteins and enzymes. Z-PHE-PRO-OH has been shown to have anti-inflammatory properties and is being investigated for its potential use in the treatment of various diseases, including cancer and autoimmune disorders. Additionally, it is used as a substrate in the synthesis of other peptides and small molecules. Overall, Z-PHE-PRO-OH plays an important role in understanding the structure and function of proteins and has potential therapeutic applications.

InChI:InChI=1/C22H24N2O5/c25-20(24-13-7-12-19(24)21(26)27)18(14-16-8-3-1-4-9-16)23-22(28)29-15-17-10-5-2-6-11-17/h1-6,8-11,18-19H,7,12-15H2,(H,23,28)(H,26,27)/t18-,19-/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 175446-63-6 proline acid chloride 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 41518-17-6 Z-Phe-O-COO-isoBu 
• 1161-13-3 N-Cbz-L-Phe 
• 147-85-3 L-proline 
• 63-91-2 L-phenylalanine 
• 870695-98-0 benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 769922-77-2 (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 17543-49-6 (S)-benzyloxycarbonylphenylalanine pentafluorophenyl ester 
• 52641-32-4 N-benzyloxycarbonyl-L-phenylalanyl chloride 
• 60746-24-9 Benzyloxycarbonyl-L-phenylalanin-seleno-phenylester 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 

Downstream Products

• 161403-98-1 Z-Phe-Pro-Gly-EtDa<*>Gly<*>Gly-Boc 
• 102988-92-1 C₂₇H₃₂N₂O₇ 
• 184296-13-7 (5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-20-((S)-1-hydroxy-ethyl)-8,14-bis-hydroxymethyl-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone 
• 184296-00-2 cyclo[D-Val-Ser(oxaz)-D-Phe-Ser(oxaz)-Phe-Pro-Allo-Thr(oxaz)] 
• 184295-99-6 (2S,8S,11S,14R,17S,20R,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone 
• 184296-14-8 (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone 
• 184296-10-4 (5S,8S,11R,14S,17S,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone 
• 184296-07-9 (5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone 
• 184295-98-5 Cbz-D-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr(oxaz)-OMe 
• 184296-05-7 Cbz-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr(oxaz)-OMe 
• 184295-97-4 Cbz-D-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr-OMe 

Relevant articles and documents

MALT1 INHIBITORS AND USES THEREOF

Provided herein are compounds of Formula (I) and pharmaceutical compositions thereof, which may be useful as MALT1 inhibitors. Also provided are for the treatment of proliferative disorders (e.g., cancer (e.g., non-Hodgkin' s lymphoma, diffuse large B-cell lymphoma, MALT lymphoma), benign neoplasm, a disease associated with angiogenesis,an autoimmune disease, an inflammatory disease, an autoinflammatory disease) by administering a compound of Formula (I).

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

Microwave irradiated high-speed solution synthesis of peptide acids employing Fmoc-amino acid pentafluorophenyl esters as coupling agents

A high-speed solution phase synthesis of peptide acids employing commercially available Fmoc-amino acid pentafluorophenyl esters as coupling agents has been demonstrated. The coupling has been found to be fast and completed in 30-45 sec. A simple work-up of the reaction mixture has resulted N-protected peptide acids in good yield. Utilizing the present method, the coupling of difficult sequences containing highly hindered α, α-dialkyl amino acids has also been demonstrated. Further, the synthesis of diastereomeric dipeptides, Fmoc-Phg-Phe-OMe and Fmoc-D-Phg-Phe-OMe revealed that the coupling is free from racemization.