Acetyl-D-alanine methyl ester
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Acetyl-D-alanine methyl ester

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Category
D-Amino Acids
Catalog number
BAT-003462
CAS number
19914-36-4
Molecular Formula
C6H11NO3
Molecular Weight
145.16
Acetyl-D-alanine methyl ester
IUPAC Name
methyl (2R)-2-acetamidopropanoate
Synonyms
Ac-D-Ala-OMe
Appearance
Yellow liquid
Purity
≥ 98% (HPLC)
Density
1.056 g/mL
Melting Point
251.1 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C6H11NO3/c1-4(6(9)10-3)7-5(2)8/h4H,1-3H3,(H,7,8)/t4-/m1/s1
InChI Key
FQGVVDYNRHNTCK-SCSAIBSYSA-N
Canonical SMILES
CC(C(=O)OC)NC(=O)C

Acetyl-D-alanine methyl ester, a versatile chemical compound with diverse applications in bioscience and industrial research, finds itself at the core of multiple key applications. Here are four distinct uses rich with perplexity and burstiness:

Peptide Synthesis: Acting as a foundational element in the chemical assembly of peptides, acetyl-D-alanine methyl ester plays a pivotal role. This protected amino acid derivative integrates seamlessly into peptide chains, enabling researchers to craft tailored peptides for delving into protein functions, enzyme intricacies, and drug discovery endeavors. The utilization of this compound unlocks a realm of possibilities for investigating complex biological processes.

Pharmaceutical Research: In the realm of drug development, acetyl-D-alanine methyl ester stands as a crucial component for the creation and evaluation of novel pharmaceutical compounds. By incorporating this ester into drug candidates, researchers enhance the stability, bioavailability, and effectiveness of therapeutic agents. This methodological approach propels the innovation of cutting-edge treatments for a spectrum of medical conditions encompassing cancer and infectious diseases.

Chiral Synthesis: Emerging as a key player in asymmetric synthesis, acetyl-D-alanine methyl ester serves as a chiral auxiliary, facilitating the generation of enantiomerically pure compounds pivotal for chiral drug and agrochemical development. Its use ensures the precise stereochemistry in chemical reactions, elevating the specificity and potency of resultant compounds. This application underscores the meticulous attention to detail and intricate chemistry involved in creating specialized molecules.

Biochemical Research: In the realm of biochemical studies, acetyl-D-alanine methyl ester emerges as a cornerstone for investigating enzyme-substrate interactions and enzyme kinetics. Through its role as a substrate or inhibitor in enzymatic reactions, researchers gain insight into the mechanisms and catalytic properties of enzymes, unraveling the complexities of biochemical pathways. This profound understanding fuels advancements in enzyme-based technologies, shaping the future of biochemical research endeavors.

1. Synthesis and cytotoxic activity of 4-O-β-D-galactopyranosyl derivatives of phenolic acids esters
Nader Al Bujuq, Sharif Arar, Raida Khalil Nat Prod Res. 2018 Nov;32(22):2663-2669. doi: 10.1080/14786419.2017.1375927. Epub 2017 Sep 18.
The glycosylation of naturally occurring phenolic acids has a significant impact on their solubility, stability and physiochemical properties. D-Galactose residue was found to form a part of glycoconjugates in several tissues and involved in a variety of physiological process. To the best of our knowledge, we have noticed a little information about the glycosylation of the phenolic acids with galactose residue. In this work, we describe the glycosylation of methyl vanillate and methyl ferulate with peracetylated-β-D-galactopyranose in the presence of BF3·OEt2. The coupling reaction yielded efficiently and selectively only the acetylated β-D-galactopyranosides 3 and 6. Removal of the acetyl groups using sodium methoxide afforded the corresponding β-D-galactopyranosides 4 and 7 in good yields. Anticancer activity in vitro was evaluated against two human cancer cell lines (MCF-7 breast cancer cell lines and PC-3 prostate cancer cell lines). β-D-galactopyranosides 4 and 7 demonstrated improved cytotoxic activity compared to the parental esters.
2. Acridinium Ester Chemiluminescence: Methyl Substitution on the Acridine Moiety
Manabu Nakazono, Shinkoh Nanbu, Takeyuki Akita, Kenji Hamase J Oleo Sci. 2021;70(11):1677-1684. doi: 10.5650/jos.ess21186.
Methyl groups were introduced on the acridine moiety in chemiluminescent acridinium esters that have electron-withdrawing groups (trifluoromethyl, cyano, nitro, ethoxycarbonyl) at the 4-position on the phenyl ester. The introduction of methyl groups at the 2-, 2,7-, and 2,3,6,7-positions on the acridine moiety shifted the optimal pH that gave relatively strong chemiluminescence intensity from neutral conditions to alkaline conditions. 4-(Ethoxycarbonyl)phenyl 2,3,6,7,10-pentamethyl-10λ4-acridine-9-carboxylate, trifluoromethanesulfonate salt showed long-lasting chemiluminescence under alkaline conditions. Acridinium esters to determine hydrogen peroxide concentration at pH 7-10 were newly developed.
3. O-Methylation of carboxylic acids with streptozotocin
Li-Yan Zeng, Yang Liu, Jiakun Han, Jinhong Chen, Shuwen Liu, Baomin Xi Org Biomol Chem. 2022 Jul 6;20(26):5230-5233. doi: 10.1039/d2ob00578f.
The clinically used DNA-alkylating drug streptozotocin (STZ) was investigated using a simple work-up as an O-methylating agent to transform various carboxylic acids, sulfonic acids and phosphorous acids into corresponding methyl esters, and did so with yields of up to 97% in 4 h at room temperature. Good substrate tolerance was observed, and benefited from the mild conditions and compatibility of the reaction with water.
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