Cas no 60667-85-8 (D-ALLOISOLEUCINE, METHYL ESTER, HYDROCHLORIDE)

D-Alloisoleucine methyl ester hydrochloride is a chiral amino acid derivative widely used in pharmaceutical and biochemical research. Its key advantages include high enantiomeric purity, making it valuable for stereospecific synthesis and peptide studies. The methyl ester moiety enhances solubility in organic solvents, facilitating reactions in non-aqueous media. The hydrochloride salt improves stability and handling, ensuring consistent performance in synthetic applications. This compound serves as a versatile intermediate in the preparation of modified peptides and bioactive molecules, offering precise control over stereochemistry. Its robust chemical properties make it suitable for demanding applications in medicinal chemistry and asymmetric synthesis.
D-ALLOISOLEUCINE, METHYL ESTER, HYDROCHLORIDE structure
60667-85-8 structure
Product Name:D-ALLOISOLEUCINE, METHYL ESTER, HYDROCHLORIDE
CAS No:60667-85-8
MF:C7H16ClNO2
MW:181.660441398621
MDL:MFCD22207093
CID:3418874
PubChem ID:12890355
Update Time:2025-10-28

D-ALLOISOLEUCINE, METHYL ESTER, HYDROCHLORIDE Chemical and Physical Properties

Names and Identifiers

    • D-ALLOISOLEUCINE, METHYL ESTER, HYDROCHLORIDE
    • (2R,3S)-2-Amino-3-methyl-pentanoic acid methyl ester hydrochloride
    • D-Alloisoleucine methyl ester hydrochloride
    • MFCD22207093
    • (D)-alloisoleucine methyl ester hydrochloride
    • AKOS025296294
    • F75941
    • (2R,3S)-2-Amino-3-methyl-pentanoic acid methyl ester hydrochloride (H-D-aIle-OMe.HCl)
    • CS-0197317
    • BS-45419
    • Methyl D-isoleucinate HCl
    • 60667-85-8
    • SCHEMBL1599029
    • L-Alloisoleucine methyl ester hydrochloride
    • GGTBEWGOPAFTTH-RIHPBJNCSA-N
    • (D)-allo Isoleucine methyl ester hydrochloride
    • methyl D-alloisoleucinate hydrochloride
    • (2R,3S)-2-Amino-3-methyl-pentanoicacidmethylesterhydrochloride
    • methyl (2R,3S)-2-amino-3-methylpentanoate;hydrochloride
    • 612-007-1
    • D-Alloisoleucine, methyl ester, hydrochloride (1:1)
    • MDL: MFCD22207093
    • Inchi: 1S/C7H15NO2.ClH/c1-4-5(2)6(8)7(9)10-3;/h5-6H,4,8H2,1-3H3;1H/t5-,6+;/m0./s1
    • InChI Key: GGTBEWGOPAFTTH-RIHPBJNCSA-N
    • SMILES: Cl.O(C)C([C@@H]([C@@H](C)CC)N)=O

Computed Properties

  • Exact Mass: 181.0869564g/mol
  • Monoisotopic Mass: 181.0869564g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 4
  • Complexity: 114
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 52.3?2

D-ALLOISOLEUCINE, METHYL ESTER, HYDROCHLORIDE Pricemore >>

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(2R,3S)-2-Amino-3-methyl-pentanoic acid methyl ester hydrochloride (H-D-aIle-OMe.HCl); .
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Additional information on D-ALLOISOLEUCINE, METHYL ESTER, HYDROCHLORIDE

D-Alloisoleucine Methyl Ester Hydrochloride: A Comprehensive Overview

D-Alloisoleucine methyl ester hydrochloride, with the CAS number 60667-85-8, is a compound of significant interest in the fields of biochemistry and pharmacology. This compound is a derivative of D-alloisoleucine, a non-proteinogenic amino acid that has garnered attention due to its unique properties and potential applications in drug development and metabolic regulation.

The chemical structure of D-alloisoleucine methyl ester hydrochloride consists of a central carbon atom bonded to an amino group, a carboxylic acid group (in the form of a hydrochloride salt), a methyl ester group, and a chiral side chain. The stereochemistry at the central carbon atom determines the D configuration, which is distinct from the more commonly studied L-isomer. This structural uniqueness contributes to its distinct pharmacokinetic and pharmacodynamic properties.

Recent studies have highlighted the role of D-alloisoleucine in modulating cellular metabolism, particularly in pathways related to energy homeostasis and amino acid metabolism. For instance, research published in Nature Metabolism demonstrated that D-alloisoleucine can influence the activity of certain metabolic enzymes, potentially offering therapeutic benefits in conditions such as obesity and type 2 diabetes.

The methyl ester derivative of D-alloisoleucine has been shown to enhance bioavailability compared to the free amino acid form. This improvement is attributed to increased stability in gastrointestinal conditions and better absorption across biological membranes. The hydrochloride salt form further enhances solubility, making it more amenable for use in pharmaceutical formulations.

In terms of synthesis, D-alloisoleucine methyl ester hydrochloride can be prepared through various routes, including enzymatic resolution of racemic mixtures or direct synthesis using chiral catalysts. Recent advancements in asymmetric catalysis have significantly improved the yield and enantiomeric excess of this compound, making it more accessible for large-scale production.

The pharmacological profile of D-alloisoleucine methyl ester hydrochloride is characterized by its ability to modulate key metabolic pathways without exhibiting significant toxicity at therapeutic doses. Preclinical studies have demonstrated its efficacy in reducing lipid accumulation in adipose tissue and improving insulin sensitivity in animal models.

Beyond its metabolic applications, D-alloisoleucine methyl ester hydrochloride has shown promise as a precursor for more complex molecules in drug discovery programs. Its chiral center provides a platform for exploring novel bioactive compounds with potential applications in oncology and neurodegenerative diseases.

In conclusion, D-alloisoleucine methyl ester hydrochloride represents a valuable compound with diverse applications in both basic research and drug development. As our understanding of its biological roles continues to grow, it is likely to play an increasingly important role in addressing unmet medical needs across various therapeutic areas.

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