13254-07-4

Basic information

• Product Name: Z-ILE-PHE-OH
• Synonyms: Z-ILE-PHE-OH;Z-L-ISOLEUCYL-L-PHENYLALANINE;CBZ-L-ILE-PHE;N-cbz-ile-phe;3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-isoleucyl]-L-alanine;Z-lle-Phe-OH;N-carbobenzyloxy-Ile-Phe;N-[N-[(Phenylmethoxy)carbonyl]-L-isoleucyl]-L-phenylalanine
• CAS NO: 13254-07-4
• Molecular Formula: C₂₃H₂₈N₂O₅
• Molecular Weight: 412.48
• EINECS: 236-242-0
• Mol File: 13254-07-4.mol

Chemical Properties

• Melting Point: 166-167 °C
• Boiling Point: 654.9 °C at 760 mmHg
• Flash Point: 349.9 °C
• Appearance: /
• Density: 1.193 g/cm³
• Vapor Pressure: 4.78E-18mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: -15°C
• PKA: 3.54±0.10(Predicted)
• CAS DataBase Reference: Z-ILE-PHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ILE-PHE-OH(13254-07-4)
• EPA Substance Registry System: Z-ILE-PHE-OH(13254-07-4)

Safety Data

• Hazardous Substances Data: 13254-07-4(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
Z-ILE-PHE-OH is used as a research compound for investigating metabolic function, protein synthesis, and enzymatic processes. Its presence in the human body and its role in various biological processes make it a valuable tool for understanding the underlying mechanisms of these functions.
Used in Pharmaceutical Development:
Z-ILE-PHE-OH is used as a potential therapeutic agent in the development of pharmaceuticals targeting metabolic disorders and protein-related diseases. Its ability to influence the synthesis and function of proteins and enzymes may offer new avenues for treatment and management of such conditions.
Used in Nutritional Supplements:
Z-ILE-PHE-OH is used as a dietary supplement to support the body's natural production of essential amino acids, hemoglobin, and the regulation of blood sugar and energy levels. Its presence in supplements may help individuals meet their nutritional needs and maintain overall health.
Used in Cosmetics and Personal Care Products:
Z-ILE-PHE-OH is used as an ingredient in cosmetics and personal care products, particularly in formulations that aim to improve skin health and promote the synthesis of collagen and elastin. Its role in protein synthesis may contribute to the maintenance of skin elasticity and overall appearance.
Used in Agricultural Applications:
Z-ILE-PHE-OH is used in agricultural research to study the effects of amino acids on plant growth and development. Its potential role in enhancing crop yields and improving plant health may lead to the development of new agricultural practices and products.

InChI:InChI=1/C23H28N2O5/c1-3-16(2)20(25-23(29)30-15-18-12-8-5-9-13-18)21(26)24-19(22(27)28)14-17-10-6-4-7-11-17/h4-13,16,19-20H,3,14-15H2,1-2H3,(H,24,26)(H,25,29)(H,27,28)/t16-,19-,20-/m0/s1

Upstream product

• 3160-59-6 N-Cbz-L-Isoleucine 
• 541-41-3 chloroformic acid ethyl ester 
• 22951-98-0 H-Ile-Phe-OH 
• 63-91-2 L-phenylalanine 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 88962-33-8 N-Benzyloxycarbonyl-L-isoleucyl-L-phenylalanin-2-bromethylester 
• 88962-26-9 L-phenylalanine 2-bromoethyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 25529-36-6 Z-Ile-OPfp 
• 67-56-1 methanol 
• 88962-42-9 N-Benzyloxycarbonyl-L-isoleucyl-L-phenylalanin-2-iodethylester 

Downstream Products

• 1027905-53-8 (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-phenyl-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 945403-82-7 2'-N-(N-benzyloxycarbonyl-L-isoleucyl-L-phenylalanyl)-amino-2'-deoxyadenosine 
• 945403-81-6 2'-N-(N-benzyloxycarbonyl-L-isoleucyl-L-phenylalanyl)-amino-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-adenosine 

Relevant articles and documents

Formation and isolation of simple, stable, acyclic di- and tripeptide hemiacetals

Di- and tripeptide aldehydes were found to undergo reaction with methanol to afford the corresponding methyl hemiacetals. These compounds, which possessed unusual stability, were isolated and characterized using NMR techniques and a chemical correlation experiment.

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.

Glycopeptide Synthesis: Selective C-terminal Deblocking and Peptide Chain Elongation of Glucosylserine Derivatives

Benzyloxycarbonyl-(Z-)serine 2-bromoethyl ester (3b) reacts with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide (14) to give the glucosylserine ester 15.After conversion into the corresponding 2-iodoethyl ester 23 the carboxylic group is deblocked selectively by reductive elimination using zinc.In this procedure the Z and the carbohydrate protective functions as well as the sensitive O-glycoside bond remain unaffected.The glycosylserine 24 is condensed with amino acid 2-bromoethyl esters 2 to form protected glycodipeptide 2-bromoethyl esters 18 which are extended to give glycotripeptide esters 25 after selective carboxyl deblocking.Whereas protected serine dipeptides 5 are glycosylated with 14 to form the conjugates 18, the glycosylation of the serine tripeptides 10 was not successful.