251316-98-0

Basic information

• Product Name: Fmoc-L-allo-isoleucine
• Synonyms: Fmoc-allo-lle-OH;(2S,3R)-2-(9H-Fluoren-9-ylmethoxycarboylamino)-3-methylpentanoic acid;Fmoc-L-allo-isoleucine;Fmoc-(2S,3R)-2-amino-3-methylpentanoic acid;Fmoc-allo-L-Ile-OH;Fmoc-L-allo-isoleucine≥ 99% (Chiral HPLC);(9H-Fluoren-9-yl)MethOxy]Carbonyl L-Allo-Ile-OH;Fmoc-L-Allo-Ile-OH
• CAS NO: 251316-98-0
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.41
• EINECS: 1592732-453-0
• Mol File: 251316-98-0.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 559.8 °C at 760 mmHg
• Flash Point: 292.4 °C
• Appearance: /
• Density: 1.207 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMF (Slightly), DMSO (Slightly)
• PKA: 3.92±0.22(Predicted)
• CAS DataBase Reference: Fmoc-L-allo-isoleucine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-allo-isoleucine(251316-98-0)
• EPA Substance Registry System: Fmoc-L-allo-isoleucine(251316-98-0)

Safety Data

• Hazardous Substances Data: 251316-98-0(Hazardous Substances Data)

Usage

Description

Fmoc-L-allo-isoleucine, also known as N-(9-fluorenylmethoxycarbonyl)-L-allo-isoleucine, is a non-natural, protected amino acid derivative. It is a white powder with unique chemical properties that make it valuable in the field of organic chemistry and pharmaceuticals. The fluorenylmethoxycarbonyl (Fmoc) group provides protection to the amino acid, which is crucial for its applications in peptide synthesis and related processes.

Uses

Used in Pharmaceutical Industry:
Fmoc-L-allo-isoleucine is used as a building block for the synthesis of various pharmaceutical compounds, particularly in the preparation of cyclic peptide antibiotics. Its unique structure allows for the creation of novel antibiotics with enhanced properties, such as increased stability, improved bioavailability, and targeted action against specific pathogens.
Used in Organic Chemistry:
In the field of organic chemistry, Fmoc-L-allo-isoleucine serves as an important intermediate for the synthesis of complex organic molecules. Its protected structure facilitates the formation of peptide bonds and other functional groups, making it a versatile component in the development of new chemical entities.
Used in Research and Development:
Fmoc-L-allo-isoleucine is also utilized in research and development for the study of protein structure, function, and interactions. Its unique properties enable scientists to investigate the role of non-natural amino acids in protein folding, stability, and biological activity, contributing to a deeper understanding of protein biology and the design of new therapeutic agents.

Upstream product

• 118878-65-2 N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine methyl ester 
• 73-32-5 L-isoleucine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 17694-98-3 L-isoleucine hydrochloride 
• 117830-88-3 Fmoc-L-Ile-OBt 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 

Downstream Products

• 113534-29-5 Fmoc-Ile-OTDO 
• 319494-39-8 Ac-VEID-CHO 
• 454705-04-5 (8S,11S,14S)-11-Benzyl-14-((S)-sec-butyl)-2-nitro-10,13,16-trioxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-5-thia-9,12,15-triaza-benzocyclotetradecene-8-carboxylic acid amide 

Relevant articles and documents

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

Fmoc-OPhth, the reagent of Fmoc protection

Fmoc-OSu has been widely used for Fmoc protection of amino groups, especially amino acids, in solid phase peptide synthesis. However, it has been recognized that Fmoc-βAla-OH is formed as a by-product via the Lossen rearrangement during the reaction. Since we reconfirmed the formation of Fmoc-βAla-OH during the preparation of Fmoc-AA-OH by Fmoc-OSu, Fmoc-OPhth was designed and synthesized as a new Fmoc reagent to avoid the formation of Fmoc-βAla-OH. Furthermore, Fmoc protection by Fmoc-OPhth and Fmoc-SPPS were evaluated. The various Fmoc-amino acids prepared by Fmoc-OPhth were carried out in good yields and these are applicable in Fmoc-SPPS.

Aqueous MW eco-friendly protocol for amino group protection

In this paper a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride is presented. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di-tert-butyl carboxylic acid or chloride acid are the only wastes produced.