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N-β-Acetyl-β-alanine methyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

β−Amino Acids

Catalog number

BAT-006042

CAS number

31295-20-2

Molecular Formula

C6H11NO3

Molecular Weight

145.16

IUPAC Name

methyl 3-acetamidopropanoate

Synonyms

Ac-β-Ala-OMe; Ac-Gly-(C#CH2)OMe; 3-(Acetylamino)propanoic acid methyl ester

Purity

95%

Density

1.1±0.1 g/cm3

InChI

InChI=1S/C6H11NO3/c1-5(8)7-4-3-6(9)10-2/h3-4H2,1-2H3,(H,7,8)

InChI Key

FDIFXCFYMLCGNA-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NCCC(=O)OC

N-β-Acetyl-β-alanine methyl ester, a versatile chemical compound with diverse applications in biosciences and beyond. Here are the key applications of N-β-Acetyl-β-alanine methyl ester presented with high perplexity and burstiness:

Pharmaceutical Synthesis: Central to drug synthesis, N-β-Acetyl-β-alanine methyl ester plays a vital role as an intermediate in producing pharmaceutical compounds. Its contribution to drug development is indispensable, facilitating the creation of medications with exceptional purity and effectiveness. Researchers harness this compound to craft active pharmaceutical ingredients, ensuring the potency and quality of therapeutic treatments.

Peptide Synthesis: In the realm of drug discovery and biochemical research, N-β-Acetyl-β-alanine methyl ester is harnessed for synthesizing peptides and peptide-like molecules crucial for various applications. By integrating this compound into peptide chains, scientists engineer molecules with specific biological functions, pivotal for studying disease mechanisms and exploring potential therapeutic strategies. These tailored peptides serve as essential tools in unraveling complex biological processes.

Biochemical Research: A cornerstone of biochemical studies, N-β-Acetyl-β-alanine methyl ester is a valuable asset for probing the structure and function of proteins. Researchers utilize this compound to modify proteins, shedding light on their mechanisms of action. This insight is key to developing innovative treatments and diagnostic methodologies, driving advancements in medical research and healthcare practices.

Flavor and Fragrance Industry: Beyond biomedical applications, N-β-Acetyl-β-alanine methyl ester finds its place in the flavor and fragrance sector as a precursor for creating diverse flavors and scents. By leveraging this compound, manufacturers can craft intricate flavor profiles and aromatic compositions, enhancing consumer products like perfumes and food additives. This utilization contributes to the sensory appeal of a wide array of goods, enriching experiences in the realms of taste and fragrance.

1. Fatty acid methyl ester from Neurospora intermedia N-1 isolated from Indonesian red peanut cake (oncom merah)

S Priatni, S Hartati, P Dewi, L B S Kardono, M Singgih, T Gusdinar Pak J Biol Sci. 2010 Aug 1;13(15):731-7. doi: 10.3923/pjbs.2010.731.737.

The objective of this study was to identify the Fatty Acid Methyl Ester (FAME) from Neurospora intermedia N-1 that isolated from Indonesian red peanut cake (oncom). FAME profiles have been used as biochemical characters to study many different groups of organisms, such as bacteria and yeasts. FAME from N. intermedia N-1 was obtained by some stages of extraction the orange spores and fractination using a chromatotron. The pure compound (1) was characterized by 500 mHz NMR (1H and 13C), FTIR and LC-MS. Summarized data's of 1H and 13C NMR spectra of compound 1 contained 19 Carbon, 34 Hydrogen and 2 Oxygen (C19H34O2). The position of the double bonds at carbon number 8 and 12 were indicated in the HMBC spectrum (2D-NMR). LC-MS spectrum indicates molecular weight of the compound 1 as 294 which is visible by the presence of protonated molecular ion [M+H] at m/z 295. Methyl esters of long chain fatty acids was presented by a 3 band pattern of IR spectrum with bands near 1249, 1199 and 1172 cm(-1). We suggested that the structure of the pure compound 1 is methyl octadeca-8,12-dienoate. The presence methyl octadeca-8,12-dienoate in N. intermedia is the first report.

2. Synthesis and NMR characteristics of N-acetyl-4-nitro, N-acetyl-5-nitro, N-acetyl-6-nitro and N-acetyl-7-nitrotryptophan methyl esters

Russell R King, Larry A Calhoun Magn Reson Chem. 2009 Mar;47(3):273-6. doi: 10.1002/mrc.2377.

N-acetyl-4-nitrotryptophan methyl ester (2), N-acetyl-5-nitrotryptophan methyl ester (3), N-acetyl-6-nitrotryptophan methyl ester (4) and N-acetyl-7-nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF(3)-methanol. Assignments of the (1)H and (13)C NMR chemical shifts were made using a combination of (1)H-(1)H COSY, (1)H-(13)C HETCOR and (1)H-(13)C selective INEPT experiments.

3. N-Hydroxy pipecolic acid methyl ester is involved in Arabidopsis immunity

Lennart Mohnike, Weijie Huang, Brigitte Worbs, Kirstin Feussner, Yuelin Zhang, Ivo Feussner J Exp Bot. 2023 Jan 1;74(1):458-471. doi: 10.1093/jxb/erac422.

The biosynthesis of N-hydroxy pipecolic acid (NHP) has been intensively studied, though knowledge on its metabolic turnover is still scarce. To close this gap, we discovered three novel metabolites via metabolite fingerprinting in Arabidopsis thaliana leaves after Pseudomonas infection and UV-C treatment. Exact mass information and fragmentation by tandem mass spectrometry (MS/MS) suggest a methylated derivative of NHP (MeNHP), an NHP-OGlc-hexosyl conjugate (NHP-OGlc-Hex), and an additional NHP-OGlc-derivative. All three compounds were formed in wild-type leaves but were not present in the NHP-deficient mutant fmo1-1. The identification of these novel NHP-based molecules was possible by a dual-infiltration experiment using a mixture of authentic NHP and D9-NHP standards for leaf infiltration followed by UV-C treatment. Interestingly, the signal intensity of MeNHP and other NHP-derived metabolites increased in ugt76b1-1 mutant plants. For MeNHP, we unequivocally determined the site of methylation at the carboxylic acid moiety. MeNHP application by leaf infiltration leads to the detection of a MeNHP-OGlc as well as NHP, suggesting MeNHP hydrolysis to NHP. This is in line with the observation that MeNHP infiltration is able to rescue the fmo1-1 susceptible phenotype against Hyaloperonospora arabidopsidis Noco 2. Together, these data suggest MeNHP as an additional storage or transport form of NHP.