L-Alanine amide hydrobromide
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L-Alanine amide hydrobromide

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Category
L-Amino Acids
Catalog number
BAT-003949
CAS number
102029-80-1
Molecular Formula
C3H8N2O·HBr
Molecular Weight
169.02
L-Alanine amide hydrobromide
IUPAC Name
(2S)-2-aminopropanamide;hydrobromide
Synonyms
L-Ala-NH2 HBr; (S)-2-Aminopropanamide hydrobromide; Propanamide,2-amino-,hydrobromide (1:1),(2S); L-Alaninamide hydrobromide
Appearance
White solid
Purity
≥ 98% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C3H8N2O.BrH/c1-2(4)3(5)6;/h2H,4H2,1H3,(H2,5,6);1H/t2-;/m0./s1
InChI Key
BYAVGTZKLGIZPY-DKWTVANSSA-N
Canonical SMILES
CC(C(=O)N)N.Br

L-Alanine amide hydrobromide, a versatile chemical compound with applications in biochemistry and pharmaceuticals, serves as a key player in various realms. Here are four crucial applications of L-Alanine amide hydrobromide presented with high perplexity and burstiness:

Peptide Synthesis: A cornerstone in peptide synthesis, L-Alanine amide hydrobromide is a multifaceted component acting as a protective group or intermediate. It plays a pivotal role in the intricate process of constructing complex peptides, ensuring precise chain assembly and stability. This compound is indispensable for the creation of peptides utilized in both research endeavors and therapeutic interventions.

Enzyme Function Studies: Delving into the realm of enzyme kinetics and interactions, researchers harness L-Alanine amide hydrobromide to elucidate the complexities of enzyme-substrate dynamics. By serving as a versatile substrate or inhibitor, it aids scientists in unraveling the catalytic mechanisms and specificities of enzymes. These studies are paramount for the development of enzyme inhibitors with potential as novel drug candidates, pushing the boundaries of pharmaceutical innovation.

Pharmaceutical Formulation: Within the domain of pharmaceutical formulation, L-Alanine amide hydrobromide plays a crucial role primarily as an excipient with stabilizing properties. It contributes to the stabilization of active pharmaceutical ingredients, enhancing their bioavailability and ensuring optimized therapeutic effects. This compound drives efficiency in drug delivery systems, elevating the efficacy of diverse pharmaceutical formulations.

Biochemical Research: In the intricate landscape of biochemical research, L-Alanine amide hydrobromide serves as a key tool for probing protein structure and function. Acting as a model compound in experiments, it facilitates the exploration of amino acid behavior and interactions in varied environments. These investigations shed light on protein folding mechanisms and stability, deepening our comprehension of fundamental biochemical processes and paving the way for groundbreaking discoveries in biophysics.

1. Potential inhibitors of L-asparagine biosynthesis. 5. Electrophilic amide analogues of (S)-2,3-diaminopropionic acid
M Mokotoff, L W Logue J Med Chem. 1981 May;24(5):554-9. doi: 10.1021/jm00137a015.
Three electrophilic amide analogues of (S)-2,3-diaminopropionic acid (1, DAP) have been prepared as potential inhibitors of L-asparagine synthetase (ASase, from Novikoff hepatoma, EC 6.3.5.4). DAP was selectively blocked by the carbobenzoxy (Cbz) group to give 3-N-Cbz-DAP (2a). Esterification of 2a with isobutylene afforded tert-butyl 3-N-carbobenzoxy-(S)-2,3-diaminopropionate (3a), which was then blocked at the 2 position with the tert-butoxycarbonyl (Boc) group to give tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-[(carbobenzoxy)amino]propionate (4). Selective cleavage of the Cbz group by H2/Pd gave the key intermediate tert-butyl 2-N-(tert-butoxycarbonyl)-(S)-2,3-diaminopropionate (5), which was acylated, via the N-hydroxysuccinimide esters, with bromoacetic acid, dichloroacetic acid, and fumaric acid monoethyl ester to give tert-butyl 2-[(S)-(tert-butoxycarbonyl)-amino]-3-(2-bromoacetamido)propionate (6a), tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-(2,2-dichloroacetamido)propionate (6b), and tert-butyl 2-[(S)-(tert-butoxycarbonyl)amino]-3-(ethoxycarbonyl)acrylamido]-propionate (6c), respectively. Deblocking of 6a-c gave the corresponding amino acids (S)-2-amino-3-(2-bromoacetamido)propionic acid hydrobromide (7a), (S)-2-amino-3-(2,2-dichloroacetamido)propionic acid (7b), and ethyl N-[(S)-2-amino-2-carboxyethyl]fumarate (7c). By a slightly different procedure, 5 was converted in two steps to (S)-2-amino-3-acetamidopropionic acid hydrobromide (7d). The inhibition of ASase by 7a-c at 1 mM was 93, 19, and 37%, respectively, while 7d was without inhibition at 2 mM. Compounds 7a-c failed to increase the life span of mice infected with B16 melanoma.
2. Highly selective kappa opioid analgesics. Synthesis and structure-activity relationships of novel N-[(2-aminocyclohexyl)aryl]acetamide and N-[(2-aminocyclohexyl)aryloxy]acetamide derivatives
C R Clark, P R Halfpenny, R G Hill, D C Horwell, J Hughes, T C Jarvis, D C Rees, D Schofield J Med Chem. 1988 Apr;31(4):831-6. doi: 10.1021/jm00399a025.
This paper describes the synthesis, structure-activity relationships (SAR) of mu and kappa opioid binding affinities, and analgesic properties of a series of novel highly selective kappa opioid N-[(2-aminocyclohexyl)aryl]acetamide and N-[(2-aminocyclohexyl)aryloxy] acetamide derivatives. Ten compounds, 14, 15, 31-37, and 39 (Tables I and II), show a marked kappa selectivity of greater than 100:1 over mu binding, with high affinity for the kappa opioid receptor (approximately 10(-8) - 10(-9) M). Compound 39, (S,S-trans)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-4-benzo[b] furanacetamide hydrobromide, has the highest mu/kappa selectivity, 780:1 (kappa Ki = 4.2 nM), reported to date. Four of these compounds, 14, 15, and their S,S-trans enantiomers, 37 and 39, respectively, produce effective analgesia by oral administration, as assayed by a rat-paw pressure test (RPP) (MPE50 = 24, 26, 8.3, and 12 mg/kg, respectively). The R,R-trans isomer, 38, was inactive in binding and RPP. The analgesic effect was reversed by administration of naloxone, confirming these effects are opioid in character. Optimal activity is produced when the basic nitrogen atom is in a pyrrolidine ring, the aryl group is a 10-pi-electron-rich aromatic system, such as 4-benzo[b]thiophene, 4-benzo[b]furan, or 4-chlorophenoxy, and overall lipophilicity lies within the range log P = 3.5-5.0.
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