17350-17-3

Basic information

• Product Name: Z-PRO-PHE-OH
• Synonyms: N-CBZ-PRO-PHE;N-CARBOBENZOXY-L-PROPYL-L-PHENYLALANINE;N-BENZYLOXYCARBONYL-L-PROLYL-L-PHENYLALANINE;Z-L-PROLYL-L-PHENYLALANINE;Z-PRO-PHE;Z-PRO-PHE-OH;3-phenyl-N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-L-alanine;N-carbobenzyloxy-Pro-Phe
• CAS NO: 17350-17-3
• Molecular Formula: C₂₂H₂₄N₂O₅
• Molecular Weight: 396.44
• EINECS: 241-374-7
• Product Categories: Amino Acid Derivatives;Dipeptides;Dipeptides and Tripeptides;Peptides
• Mol File: 17350-17-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 653.6 °C at 760 mmHg
• Flash Point: 349.1 °C
• Appearance: /
• Density: 1.291 g/cm³
• Vapor Pressure: 5.68E-18mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-PRO-PHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PRO-PHE-OH(17350-17-3)
• EPA Substance Registry System: Z-PRO-PHE-OH(17350-17-3)

Safety Data

• Hazardous Substances Data: 17350-17-3(Hazardous Substances Data)

Usage

Description

Z-PRO-PHE-OH is a synthetic chemical compound composed of the amino acids proline (PRO) and phenylalanine (PHE), connected by a peptide bond. It serves as a fundamental building block in the synthesis of peptides and proteins, renowned for its stability and compatibility with a wide range of chemical reactions. This makes Z-PRO-PHE-OH an indispensable tool in peptide chemistry, particularly in research and pharmaceutical settings for the development of peptide-based drugs and therapies. Its potential extends to the study of protein structure and function, as well as the design and engineering of new peptides with tailored properties and activities.

Uses

Used in Pharmaceutical Industry:
Z-PRO-PHE-OH is used as a key component in the development of peptide-based drugs and therapies due to its stability and compatibility with various chemical reactions. It aids in the creation of new pharmaceutical agents with specific therapeutic targets and properties.
Used in Peptide Chemistry Research:
In the field of peptide chemistry, Z-PRO-PHE-OH is utilized as a building block for the synthesis of complex peptide structures. Its stability and reactivity make it a valuable asset in the design and synthesis of novel peptides with unique biological activities.
Used in Protein Structure and Function Studies:
Z-PRO-PHE-OH is employed in research aimed at understanding the structure and function of proteins. By incorporating this compound into peptide sequences, scientists can probe and manipulate protein conformation and activity, leading to insights into protein dynamics and mechanisms of action.
Used in Peptide Design and Engineering:
Z-PRO-PHE-OH is used as a versatile component in the design and engineering of new peptides with specific properties and activities. Its incorporation allows for the creation of peptides with tailored characteristics, such as enhanced stability, selectivity for targets, or novel biological functions, which can be applied across various industries and research areas.

InChI:InChI=1/C22H24N2O5/c25-20(23-18(21(26)27)14-16-8-3-1-4-9-16)19-12-7-13-24(19)22(28)29-15-17-10-5-2-6-11-17/h1-6,8-11,18-19H,7,12-15H2,(H,23,25)(H,26,27)/t18-,19-/m0/s1

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 
• 105414-01-5 Cbz-L-Pro-OCO₂-i-Bu 
• 886981-23-3 benzyl (2S)-2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)tetrahydro-1H-pyrrole-1-carboxylate 
• 23631-72-3 N-carbobenzoxy-L-prolyl-L-phenylalanine methyl ester 

Downstream Products

• 6464-80-8 N-carbobenzoxy-L-prolyl-L-phenylalanyl-N^ω-nitro-L-arginine methyl ester 
• 88105-58-2 N-carbobenzoxy-L-prolyl-L-phenylalanine 3-(carbobenzoxyamino)propylamide 
• 92278-80-3 Z-Pro-Phe-OBzl-SO₃Na 
• 13589-02-1 L-prolyl-L-phenylalanine 
• 127861-61-4 N-(1-benzyloxycarbonyl-L-prolyl)-L-phenylalanin-amide 
• 28607-52-5 1-benzyloxycarbonyl-L-prolyl=>L-phenylalanyl=>L-histidyl=>L-leucine methyl ester 
• 1400991-77-6 (S)-N-{(R)-1-[3-(3,5-bis(trifluoromethyl)phenyl)ureido]-2-phenylethyl}pyrrolidine-2-carboxamide 

Relevant articles and documents

Combining prolinamides with 2-pyrrolidinone: Novel organocatalysts for the asymmetric aldol reaction

Peptides and especially prolinamides have been identified as excellent organocatalysts for the aldol reaction. The combination of prolinamides with derivatives bearing the 2-pyrrolidinone scaffold, deriving from pyroglutamic acid, led to the identification of novel organocatalysts for the intermolecular asymmetric aldol reaction. The new hybrids were tested both in organic and aqueous media. Among the compounds tested, 22 afforded the best results in petroleum ether, while 25 afforded the products in brine in high yields and selectivities. Then, various ketones and aldehydes were utilized and the products of the aldol reaction were obtained in high yields (up to 100%) with excellent diastereo- (up to 97:3 dr) and enantioselectivities (up to 99% ee).

Direct Hydroxylation of Benzene to Phenol by Cytochrome P450BM3 Triggered by Amino Acid Derivatives

The selective hydroxylation of benzene to phenol, without the formation of side products resulting from overoxidation, is catalyzed by cytochrome P450BM3 with the assistance of amino acid derivatives as decoy molecules. The catalytic turnover rate and the total turnover number reached 259 min?1 P450BM3?1 and 40 200 P450BM3?1 when N-heptyl-l-proline modified with l-phenylalanine (C7-l-Pro-l-Phe) was used as the decoy molecule. This work shows that amino acid derivatives with a totally different structure from fatty acids can be used as decoy molecules for aromatic hydroxylation by wild-type P450BM3. This method for non-native substrate hydroxylation by wild-type P450BM3 has the potential to expand the utility of P450BM3 for biotransformations.

Novel prolinamide-ureas as organocatalysts for the asymmetric aldol reaction

Among the various versions of the aldol reaction, the enantioselective reaction between cyclic ketones and aldehydes constitutes a typical reaction model for the evaluation of novel organocatalysts. A multifunctional organocatalyst consisting of a prolinamide moiety, a gem diamine unit and a urea group was successfully employed in this asymmetric transformation. The products of the reaction between various ketones and aldehydes were obtained in high yields (up to 98%) with excellent diastereo- (up to >98:2 dr) and enantioselectivities (up to 99% ee).