2577-46-0

Basic information

• Product Name: Methyl L-isoleucinate
• Synonyms: methyl L-isoleucinate;(3S)-3-Methyl-L-norvaline methyl ester;(3S)-L-Isoleucine methyl ester;L-Isoleucine methyl;(2S,3S)-methyl 2-amino-3methylpentanoate;(2S,3S)-2-Amino-3-methylpentanoic acid methyl ester
• CAS NO: 2577-46-0
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.2
• EINECS: 219-931-0
• Mol File: 2577-46-0.mol

Chemical Properties

• Boiling Point: 169.203 °C at 760 mmHg
• Flash Point: 42.685 °C
• Appearance: /
• Density: 0.955 g/cm³
• Vapor Pressure: 1.56mmHg at 25°C
• Refractive Index: 1.435
• Storage Temp.: 2-8°C
• PKA: 7.98±0.39(Predicted)
• CAS DataBase Reference: Methyl L-isoleucinate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl L-isoleucinate(2577-46-0)
• EPA Substance Registry System: Methyl L-isoleucinate(2577-46-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2577-46-0(Hazardous Substances Data)

Usage

Uses

Used in the Chemical Industry:
Methyl L-isoleucinate is used as a building block for the synthesis of various chemical compounds, such as polymers and pharmaceuticals. Its unique structure allows it to be a valuable component in the development of new materials with specific properties.
Used in the Polymer Industry:
Methyl L-isoleucinate is used as a monomer in the preparation method of polybutylene succinate. This application takes advantage of its ability to form polymers with desirable characteristics, such as biodegradability and mechanical strength, making it a promising candidate for sustainable and eco-friendly materials.

InChI:InChI=1/C7H15NO2/c1-4-5(2)6(8)7(9)10-3/h5-6H,4,8H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 319-78-8 D-Isoleucine 
• 1356449-88-1 calyxamide B 
• 73-32-5 L-isoleucine 
• 17901-01-8 N-(tert-butoxycarbonyl)isoleucine methyl ester 
• 13139-16-7 N-(tert-butyloxycarbonyl)-L-isoleucine 
• 610800-47-0 (2S,3S)-methyl 3-methyl-2-(4-nitrophenylsulphonamido)pentanoate 
• 1169571-12-3 aspereline A 
• 1169571-13-4 aspereline B 
• 1169571-14-5 aspereline C 
• 1169571-16-7 aspereline E 
• 1169571-17-8 aspereline F 
• 1356449-87-0 calyxamide A 
• 1420846-00-9 metatacarboline G 

Downstream Products

• 78569-25-2 Z-L-Leu-D-Ileu-OH 
• 20807-11-8 ((benzyloxy)carbonyl)glycyl-L-isoleucine 
• 27482-73-1 ZTyrIleOMe 
• 5254-68-2 N-(N,O-bis-benzyloxycarbonyl-L-tyrosyl)-L-isoleucine methyl ester 
• 122242-36-8 S-benzyl-N-benzyloxycarbonyl-L-cysteinyl=>L-phenylalanyl=>L-isoleucine methyl ester 
• 86961-90-2 S-benzyl-N-benzyloxycarbonyl-cysteinyl=>tyrosyl=>isoleucine methyl ester 
• 102320-12-7 N-(O-acetyl-N-formyl-L-tyrosyl)-L-isoleucine methyl ester 
• 42537-96-2 N-(N-benzyloxycarbonyl-L-leucyl)-L-isoleucine 
• 121467-96-7 S-benzyl-N-(toluene-4-sulfonyl)-cysteinyl=>tyrosyl=>isoleucine methyl ester 
• 14445-54-6 L-isoleucinamide 
• 59189-00-3 N-carbobenzyloxy-L-tryptophanyl-L-isoleucine methyl ester 
• 4817-98-5 Z-Leu-Ile-OMe 
• 4474-95-7 N-(benzyloxycarbonyl)-L-phenylalanyl-L-isoleucine methyl ester 
• 4818-04-6 Z-Ile-Ile-OMe 

Relevant articles and documents

Synthesis and evaluation of antitumor activities of 4-selenopyrimidine derivatives

Pyrimidine antimetabolic agents are the essential drugs in treatment of various tumors. Novel synthesis and biological evaluation of the pyrimidine derivatives incorporating selenium element and amino acid carrier as potential antitumor agents have not been tried and studied. Based on the biological significance of pyrimidine structure, these two additional elemental fragments maybe enhance the antitumor effect and reduce toxic side effects of pyrimidine agents. The aim of this paper is to synthesis a series of 4-selenopyrimidine derivatives in order to find more potent lead compounds against cancer. In this study, 12 new 4-selenopyrimidine derivatives that are unstable in acidic solutions but very stable in alkaline and neutral solutions avoiding light were synthesized, and the antitumor activities on HepG2 cell lines of these compounds were evaluated by MTT assay. The results have shown that these compounds could reduce the proliferation of HepG2 cells in a dose-dependent fashion, and the inhibitory activity of compounds a6 was greater than that of positive control 5-fluorouracil (5-FU), the IC50 for a6 was 3.63 μM. In the comprehensive analysis of the structure–activity relationship, we could draw the antitumor effect of selenouracil derivatives is stronger than those of selenothymine derivatives. These results suggest that the substituent groups of selenium element and amino acid on the pyrimidine derivatives are vital for their antitumor activities on HepG2 cells.

N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers

Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.

Cleavable Amide Bond: Mechanistic Insight into Cleavable 4-Aminopyrazolyloxy Acetamide at Low pH

The cleavage of amide bonds under mild acidic conditions is a rare chemical event. N-Acetamide bond of peptides is extremely stable even under the strongest organic acid trifluoromethanesulfonic acid. This report mechanistically describes a new cleavable amide bond in 4-aminopyrazolyloxy acetamide peptide analogues under mild acidic conditions such as trifluoroacetic acid (10-20%) or HCl (0.1-4.0 N) at room temperature, and the formation of unusual lactam from 4-aminopyrazolyloxy acetic acid after evaporation of solvent. This is a rare chemical event in peptide bond, which could be explored as acid-sensitive protecting group of free amines.

Cleavable Amide Bond: Mechanistic Insight into Cleavable 4-Aminopyrazolyloxy Acetamide at Low pH

The cleavage of amide bonds under mild acidic conditions is a rare chemical event. N-Acetamide bond of peptides is extremely stable even under the strongest organic acid trifluoromethanesulfonic acid. This report mechanistically describes a new cleavable amide bond in 4-aminopyrazolyloxy acetamide peptide analogues under mild acidic conditions such as trifluoroacetic acid (10-20%) or HCl (0.1-4.0 N) at room temperature, and the formation of unusual lactam from 4-aminopyrazolyloxy acetic acid after evaporation of solvent. This is a rare chemical event in peptide bond, which could be explored as acid-sensitive protecting group of free amines.

Heterocyclic Compounds from the Mushroom Albatrellus confluens and Their Inhibitions against Lipopolysaccharides-Induced B Lymphocyte Cell Proliferation

Eight hetereocyclic compounds conflamides B-I with an unprecedented skeleton and their precursor conflamide A were isolated from the mushroom Albatrellus confluens. Their structures and absolute configurations were determined by use of NMR studies, total synthesis, and calculated ECD spectra. Conflamides D and E were found to exhibit potent inhibition against LPS-induced B lymphocyte cell proliferation with IC50 values 1.48 and 5.71 μM, respectively.

Simple and efficient Fmoc removal in ionic liquid

A mild method for an efficient removal of the fluorenylmethoxycarbonyl (Fmoc) group in ionic liquid was developed. The combination of a weak base such as triethylamine and [Bmim][BF4] makes the entire system more efficient for the cleavage at room temperature of various amines and amino acid methyl esters in short reaction times. The procedure works well even in the case of N-Fmoc amino acids bearing acid-sensitive protecting groups and of N-alkylated amino acid methyl esters. The solvent-free condition provides a complementary method for Fmoc deprotection in solution phase peptide synthesis and modern organic synthesis.

COMPOUND, COMPOSITION AND USES THEREOF

The compositions and compounds of formula I, formula II, formula III which includes a salt of polyunsaturated fatty acids in a molecular conjugate with amino acid isoleucine or its polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These salts may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection administration. Such compositions may be used to treatment of hyperglycemia, metabolic syndrome, diabetes, pre-diabetes, lowering triglycerides or its associated complications.

Hydroxy-Directed Amidation of Carboxylic Acid Esters Using a Tantalum Alkoxide Catalyst

We describe herein a new strategy for the chemoselective synthesis of amides by using a metal-catalyzed hydroxy-directed reaction. A hydroxy group located at the β-position of an ester group promoted the activation of a carbonyl group with a tantalum alkoxide catalyst followed by amidation reactions, leading to a wide variety of β-hydroxyamides with excellent chemeselectivity. The chemoselective amidation strategy can be extended to the catalytic synthesis of dipeptide derivatives, which remains challenging research subjects in modern organic synthesis.

Synthesis and biological evaluation of novel lipoamino acid derivatives

Seven novel lipoamino acid conjugates were synthesized from methyl oleate and amino acids. Methyl oleate was grafted to different amino acids using thioglycolic acid as a spacer group. Seven derivatives (3a-g) were prepared and characterized by spectral data (NMR, IR and MS spectral studies). All the derivatives were studied for their antimicrobial, anti-biofilm and anticancer activities. Among all the derivatives, it was found that compound 3b was the most potent antibacterial compound which showed good activity against four Gram positive bacterial strains and also exhibited excellent antifungal activity against a fungal strain. In the anti-biofilm assay, compound 3b showed promising activity with IC50 value of 2.8 μM against Bacillus subtilis MTCC 121. All the compounds showed anticancer activities with 3c showing promising anticancer activity (IC50 = 15.3-22.4 μM) against the four cell lines tested.

Pd-catalyzed coupling of γ-C(sp3)-H bonds of oxalyl amide-protected amino acids with heteroaryl and aryl iodides

Pd-catalyzed regioselective coupling of γ-C(sp3)-H bonds of oxalyl amide-protected amino acids with heteroaryl and aryl iodides is reported. A wide variety of iodides are tolerated, giving the corresponding products in moderate to good yields. Various oxalyl amide-protected amino acids were compatible in this C-H transformation, thus representing a practical method for constructing non-natural amino acid derivatives.