20807-11-8

Basic information

• Product Name: Z-GLY-ILE-OH
• Synonyms: N-BENZYLOXYCARBONYLGLYCYL-L-ISOLEUCINE;N-CARBOBENZOXY-GLYCYL-L-ISOLEUCINE;Z-GLY-ILE;Z-GLY-ILE-OH;Z-GLYCYL-L-ISOLEUCINE;N-cbz-gly-ile;N-[[(phenylmethoxy)carbonyl]glycyl]-L-isoleucine;N-carbobenzyloxy-Gly-Ile
• CAS NO: 20807-11-8
• Molecular Formula: C₁₆H₂₂N₂O₅
• Molecular Weight: 322.36
• EINECS: 244-050-3
• Mol File: 20807-11-8.mol

Chemical Properties

• Boiling Point: 582°Cat760mmHg
• Flash Point: 305.8°C
• Appearance: /
• Density: 1.203g/cm³
• Vapor Pressure: 2.17E-14mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: −20°C
• CAS DataBase Reference: Z-GLY-ILE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLY-ILE-OH(20807-11-8)
• EPA Substance Registry System: Z-GLY-ILE-OH(20807-11-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 20807-11-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Z-GLY-ILE-OH is used as a building block for the synthesis of peptides and complex molecules, contributing to the development of new drugs and treatments. Its unique "Z" configuration enhances the stability and reactivity of the compound, making it a valuable component in the creation of therapeutic agents.
Used in Biochemical Research:
In the field of biochemical research, Z-GLY-ILE-OH is employed as a model compound to study peptide synthesis, protein folding, and enzyme mechanisms. Its dipeptide structure allows researchers to investigate the fundamental principles of peptide bond formation and the interactions between amino acids, providing insights into the broader understanding of protein structure and function.
Used in Peptide Synthesis:
Z-GLY-ILE-OH is utilized as a key component in the synthesis of larger peptides and proteins. Its presence in the synthesis process helps to control the formation of peptide bonds, ensuring the correct sequence and conformation of the resulting peptide. This is particularly important in the development of peptide-based drugs, where the specific structure and function of the peptide are crucial for therapeutic efficacy.
Used in Drug Delivery Systems:
In drug delivery systems, Z-GLY-ILE-OH can be incorporated into the design of peptide-based drug carriers, enhancing the stability, solubility, and bioavailability of therapeutic agents. Its "Z" configuration may also contribute to the controlled release of drugs, allowing for a more targeted and efficient delivery of medications to specific tissues or cells.

InChI:InChI=1/C16H22N2O5/c1-3-11(2)14(15(20)21)18-13(19)9-17-16(22)23-10-12-7-5-4-6-8-12/h4-8,11,14H,3,9-10H2,1-2H3,(H,17,22)(H,18,19)(H,20,21)

Upstream product

• 73-32-5 L-isoleucine 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 2899-60-7 Cbz-Gly-ONSuc 
• 16859-24-8 Benzyloxycarbonylamino-acetic acid 3-ethylcarbamoyl-2-hydroxy-phenyl ester 
• 2577-46-0 L-isoleucine methyl ester 
• 15050-24-5 N-(benzyloxycarbonyl)glycyl chloride 
• 319-78-8 isoleucine 
• 1738-86-9 Z-Gly-ONp 

Downstream Products

• 151545-27-6 N-benzyloxycarbonylglycyl-L-isoleucylglycine benzyl ester 
• 1350624-55-3 C₂₄H₃₄N₄O₇ 
• 175918-20-4 (S)-2-({(R)-1-[(2S,3S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-pentanoylamino]-2-phenyl-ethyl}-methoxy-phosphinoyloxy)-3-phenyl-propionic acid 3-pyridin-4-yl-propyl ester 

Relevant articles and documents

SYNTHESIS OF A-AMANITIN AND ITS DERIVATIVES

The present invention relates to the chemical synthesis of α-amanitin and its derivatives. The present invention also relates to intermediate products of the α-amanitin synthesis.

SYNTHESIS OF AMANIN AND ITS DERIVATIVES

The present invention relates to the chemical synthesis of amanin and its derivatives. The present invention also relates to intermediate products of the amanin synthesis.

A Convergent Total Synthesis of the Death Cap Toxin α-Amanitin

The toxic bicyclic octapeptide α-amanitin is mostly found in different species of the mushroom genus Amanita, with the death cap (Amanita phalloides) as one of the most prominent members. Due to its high selective inhibition of RNA polymerase II, which is directly linked to its high toxicity, particularly to hepatocytes, α-amanitin received an increased attention as a toxin-component of antibody-drug conjugates (ADC) in cancer research. Furthermore, the isolation of α-amanitin from mushrooms as the sole source severely restricts compound supply as well as further investigations, as structure–activity relationship (SAR) studies. Based on a straightforward access to the non-proteinogenic amino acid dihydroxyisoleucine, we herein present a robust total synthesis of α-amanitin providing options for production at larger scale as well as future structural diversifications.

PEPTIDE BOND FORMATION UNDER PHASE-TRANSFER CONDITIONS. EFFECT OF AMINO ACID STRUCTURE

The extraction of amino acids NH2CH(R)COOH in the two-phase system consisting of 1-butanol and an amino acid buffer solution in the presence of cetyltrimethylammonium bromide and also the kinetics of the aminolysis of N-benzyloxycarbonylglycine p-nitrophe