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Catalog Number:
02620
CAS Number:
1492-11-1
Acetyl-L-leucine methyl ester
Purity:
≥ 99% (HPLC)
Synonym(s):
Ac-L-Leu-OMe, (S-Ac-2-amino-4-methylpentanoic acid methyl ester
Documents
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Product Information

Acetyl-L-leucine methyl ester (methyl (2S)-2-acetamido-4-methylpentanoate) is an N-acetylated, C-terminally esterified derivative of the branched-chain amino acid L-leucine, with a molecular formula of C9H17NO3 and a molecular weight of 187.24. The structure incorporates an acetamide-protected α-amino group and a methyl esterified carboxyl group, yielding a neutral, non-zwitterionic amino acid derivative under physiological pH. Its defined stereochemistry at the α-carbon (2S configuration) preserves the chiral center characteristic of proteinogenic L-leucine, making it suitable for stereospecific studies. The combination of moderate polarity (TPSA 55.4) and ester functionality supports solubility and compatibility in common organic and mixed aqueous-organic systems used in analytical workflows.

This compound functions as a useful building block and model substrate in peptide chemistry, amino acid modification studies, and enzymatic reaction profiling. The N-acetyl and methyl ester protecting groups provide controlled reactivity, enabling selective transformations at the side chain or backbone under tailored conditions. Its compact structure and well-defined functional groups make it a convenient reference in chromatographic method development for protected amino acid derivatives. Researchers can also employ acetyl-L-leucine methyl ester in structure–activity investigations and in optimizing conditions for deprotection, coupling, and derivatization strategies in synthetic and analytical laboratories.

Synonyms
Ac-L-Leu-OMe, (S-Ac-2-amino-4-methylpentanoic acid methyl ester
CAS Number
1492-11-1
Purity
≥ 99% (HPLC)
Molecular Formula
C9H17NO3
Molecular Weight
187.2
MDL Number
MFCD00038292
PubChem ID
559809
Optical Rotation
[a]D = -42±1º (c=3.8 in MeOH)
Conditions
Store at RT
General Information
Synonyms
Ac-L-Leu-OMe, (S-Ac-2-amino-4-methylpentanoic acid methyl ester
CAS Number
1492-11-1
Purity
≥ 99% (HPLC)
Molecular Formula
C9H17NO3
Molecular Weight
187.2
MDL Number
MFCD00038292
PubChem ID
559809
Optical Rotation
[a]D = -42±1º (c=3.8 in MeOH)
Conditions
Store at RT
Properties
Additional property information coming soon!
-
Safety and Regulations
Hazmat
No
Antibiotic
No
DEA-regulated
No
Warnings
-
Applications

Acetyl-L-leucine methyl ester is a protected amino acid derivative useful as a model substrate, building block, and analytical standard in peptide and amino acid research workflows.

  • Protected amino acid building block The N-acetyl and methyl ester functionalities allow its use as a selectively activatable unit in peptide-related synthetic sequences and optimization studies.
  • Chromatographic method development Its well-defined polarity and protected functional groups make it a suitable test analyte for developing and calibrating HPLC or LC-based methods for amino acid derivatives.
  • Enzymatic specificity studies The acetamide and methyl ester groups enable investigation of enzyme preferences toward N-acylated and esterified leucine substrates in hydrolysis or acyl-transfer assays.
  • Structure–activity relationship (SAR) models As an N-acetylated, esterified L-leucine analogue, it can serve in SAR studies probing the impact of backbone protection on recognition by biomolecular targets in vitro.
  • Derivatization and deprotection optimization The compound is suitable for testing conditions and reagents for selective cleavage or transformation of acyl and ester protecting groups in method development.
  • Reference compound for chiral analysis Its defined 2S stereochemistry makes it useful as a reference material when evaluating chiral separation or stereoselective reaction conditions involving leucine derivatives.

Citations