71989-23-6

Basic information

• Product Name: FMOC-L-Isoleucine
• Synonyms: Fmoc-Ile-OH >=98.0% (T);Fmoc-(2S,3S)-2-amino-3-methylpentanoic acid;Fmoc-L-isoleucine≥ 99% (HPLC);N-FMOC-L-ISOLEUCINE;N-FMOC-ILE-OH;Fmoc-lle-OH;L-Isoleucine, FMOC protected;N-FMOC-ILE-OH ( N-FMOC-L-ISOLEUCINE)
• CAS NO: 71989-23-6
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.41
• EINECS: 276-255-9
• Product Categories: Protected Amino Acids;Fluorenes, Flurenones;AMINOACIDS DERIVATIVES;Amino Acids;Isoleucine [Ile, I];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
• Mol File: 71989-23-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 145-147 °C(lit.)
• Boiling Point: 486.83°C (rough estimate)
• Flash Point: 292.4 °C
• Appearance: White/Fine Crystalline Powder
• Density: 1.2107 (rough estimate)
• Vapor Pressure: 2.28E-13mmHg at 25°C
• Refractive Index: -12 ° (C=1, DMF)
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol (very faint turbidity).
• PKA: 3.92±0.22(Predicted)
• BRN: 4716717
• CAS DataBase Reference: FMOC-L-Isoleucine(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-Isoleucine(71989-23-6)
• EPA Substance Registry System: FMOC-L-Isoleucine(71989-23-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26
• WGK Germany: 3
• Hazardous Substances Data: 71989-23-6(Hazardous Substances Data)

Usage

Chemical Properties

white fine crystalline powder

Uses

N-Fmoc-L-isoleucine is an unnatural amino acid used for peptidomimetics. It is also used as a pharmaceutical intermediate.

General Description

The product number for this product was previously 04-12-1024.To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

InChI:InChI=1/C21H23NO4/c1-3-13(2)19(20(23)24)22-21(25)26-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,13,18-19H,3,12H2,1-2H3,(H,22,25)(H,23,24)/t13-,19-/m1/s1

Upstream product

• 73-32-5 L-isoleucine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 251316-98-0 Fmoc-Ile 
• 117830-88-3 Fmoc-L-Ile-OBt 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 17694-98-3 L-isoleucine hydrochloride 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 

Downstream Products

• 263841-90-3 (2S,3S)-2-{(2S,3S)-2-[(S)-2-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-4-carbamoyl-butyrylamino]-3-(1H-indol-3-yl)-propionylamino]-3-methyl-pentanoylamino}-3-methyl-pentanoic acid 
• 175548-82-0 N-Fmoc-Ile-Phe-Ser(Bu^t)-Pro-Ile-Pro-OBu^t 
• 82007-11-2 Fmoc-Ile-OTcp 
• 103321-51-3 ((1S,2S)-1-Chlorocarbonyl-2-methyl-butyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 73-32-5 L-isoleucine 
• 143038-24-8 (2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-pentanoic acid 4-(2-oxo-2-phenyl-ethoxycarbonylmethoxy)-benzyl ester 
• 86060-89-1 N-α-Fmoc-L-isoleucine pentafluorophenyl ester 
• 113534-29-5 Fmoc-Ile-OTDO 

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.