Acetyl-D-phenylalanine methyl ester
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Acetyl-D-phenylalanine methyl ester

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Category
D-Amino Acids
Catalog number
BAT-003466
CAS number
21156-62-7
Molecular Formula
C12H15NO3
Molecular Weight
221.30
Acetyl-D-phenylalanine methyl ester
IUPAC Name
methyl (2R)-2-acetamido-3-phenylpropanoate
Synonyms
Ac-D-Phe-Ome; methyl n-acetyl-d-phenylalaninate
Appearance
White powder
Purity
≥ 99% (TLC)
Density
1.117±0.06 g/cm3(Predicted)
Melting Point
86-92 °C
Boiling Point
391.0±30.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C12H15NO3/c1-9(14)13-11(12(15)16-2)8-10-6-4-3-5-7-10/h3-7,11H,8H2,1-2H3,(H,13,14)/t11-/m1/s1
InChI Key
IKGHIFGXPVLPFD-LLVKDONJSA-N
Canonical SMILES
CC(=O)NC(CC1=CC=CC=C1)C(=O)OC
1. 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.
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. 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.
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