Acetyl-L-alanine methyl amide
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Acetyl-L-alanine methyl amide

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Category
L-Amino Acids
Catalog number
BAT-003905
CAS number
19701-83-8
Molecular Formula
C6H12N2O2
Molecular Weight
144.18
Acetyl-L-alanine methyl amide
IUPAC Name
(2S)-2-acetamido-N-methylpropanamide
Synonyms
Ac-L-Ala-NHMe; (S)-2-Acetamido-N-methylpropanamide
Appearance
White powder
Purity
≥ 99% (TLC)
Density
1.031g/cm3
Melting Point
179-183 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C6H12N2O2/c1-4(6(10)7-3)8-5(2)9/h4H,1-3H3,(H,7,10)(H,8,9)/t4-/m0/s1
InChI Key
VHCVPWSUVMHJLL-BYPYZUCNSA-N
Canonical SMILES
CC(C(=O)NC)NC(=O)C

Acetyl-L-alanine methyl amide, a synthetic peptide derivative with diverse applications in biosciences and medicine, is a versatile compound. Here are the key applications of Acetyl-L-alanine methyl amide, presented with high perplexity and burstiness:

Peptide Synthesis: A cornerstone in peptide synthesis, Acetyl-L-alanine methyl amide serves as a fundamental building block. It facilitates the creation of tailored peptides essential for drug discovery and research endeavors. Researchers leverage this compound to craft peptides with precise sequences and characteristics tailored for therapeutic and experimental applications.

Drug Development: In the pharmaceutical realm, this compound plays a pivotal role in designing and formulating enzyme inhibitors. By integrating Acetyl-L-alanine methyl amide into drug structures, researchers can engineer compounds that effectively hinder target enzymes implicated in disease pathways. This innovative approach holds promise for developing treatments spanning diverse conditions like cancer, viral infections, and metabolic disorders.

Biochemical Research: Acetyl-L-alanine methyl amide emerges as a potent tool in biochemical investigations, aiding in unraveling the intricacies of protein structure and function. It seamlessly integrates into peptide chains, mimicking specific protein regions. This enables researchers to probe protein interactions and folding mechanisms, potentially uncovering novel insights into protein behavior and paving the way for innovative therapeutic interventions.

Biotechnology: In the dynamic field of biotechnology, Acetyl-L-alanine methyl amide finds extensive utility in the manufacturing of recombinant proteins. By incorporating this compound into expression systems, protein stability and solubility can be enhanced significantly. This application holds critical significance in producing premium-grade proteins essential for industrial, medical, and research applications, propelling advancements in biotechnological frontiers.

1. Neural-network analysis of the vibrational spectra of N-acetyl L-alanyl N'-methyl amide conformational states
H G Bohr, K Frimand, K J Jalkanen, R M Nieminen, S Suhai Phys Rev E Stat Nonlin Soft Matter Phys. 2001 Aug;64(2 Pt 1):021905. doi: 10.1103/PhysRevE.64.021905. Epub 2001 Jul 20.
Density-functional theory (DFT) calculations utilizing the Becke 3LYP hybrid functional have been carried out for N-acetyl L-alanine N'-methylamide and examined with respect to the effect of water on the structure, the vibrational frequencies, vibrational absorption (VA), vibrational circular dichroism (VCD), Raman spectra, and Raman optical activity (ROA) intensities. The large changes due to hydration in the structures, and the relative stability of the conformer, reflected in the VA, VCD, Raman spectra, and ROA spectra observed experimentally, are reproduced by the DFT calculations. A neural network has been constructed for reproducing the inverse scattering data (we infer the structural coordinates from spectroscopic data) that the DFT method could produce. The purpose of the network has also been to generate the large set of conformational states associated with each set of spectroscopic data for a given conformer of the molecule by interpolation. Finally the neural network performances are used to monitor a sensitivity analysis of the importance of secondary structures and the influence of the solvent. The neural network is shown to be good in distinguishing the different conformers of the small alanine peptide, especially in the gas phase.
2. Energetics of the deformation of a peptide unit. Semi-empirical molecular orbital and ab initio study of N-methyl acetamide and N-acetyl-L-alanine N-methyl amide
V Renugopalakrishnan, R Rein Biochim Biophys Acta. 1976 May 20;434(1):164-8. doi: 10.1016/0005-2795(76)90046-5.
The problem of non-planarity of peptide unit has been investigated using N-methyl acetamide as a theoretical model. A semi-empirical molecular orbital method: Iterative Extended Hückel Theory viz. IEHT/2 (Adams S. (1974) Doctoral dissertation, State University of New York at Buffalo, U.S.A.) and non-empirical abinitio method with minimal basis set, STO-3G (Hehre, W.J., Stewart, R.F. and Pople, J.A. (1969) J. Chem. Phys. 51, 2657-2664) were used to probe the energetics of the distortion of a planar peptide unit. Distortion of one of the peptide units in a dipeptide, N-acetyl-L-alanine N-methyl amide has also been investigated using abinitio method. The studies amply demonstrate the possibility of the existence of a non-planar peptide unit. Distortion of about 10-15 degrees is predicted to bring about very small loss in energy. The results are substantiated by results from experimental studies.
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