Formyl-L-alanine methyl ester
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Formyl-L-alanine methyl ester

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Category
L-Amino Acids
Catalog number
BAT-003935
CAS number
32221-83-3
Molecular Formula
C5H9NO3
Molecular Weight
131.13
Formyl-L-alanine methyl ester
IUPAC Name
methyl (2S)-2-formamidopropanoate
Synonyms
For-L-Ala-OMe; Alanine,N-formyl-,methyl ester (6CI,7CI); N-Formyl-L-alanine methyl ester; Alanine,N-formyl-,methyl ester,L-(8CI); Formyl-L-alanine methyl ester
Appearance
White powder
Purity
≥ 99% (TLC)
Density
1.083±0.06 g/cm3
Boiling Point
92-94 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C5H9NO3/c1-4(6-3-7)5(8)9-2/h3-4H,1-2H3,(H,6,7)/t4-/m0/s1
InChI Key
SVSWJSUDUWAMGX-BYPYZUCNSA-N
Canonical SMILES
CC(C(=O)OC)NC=O

Formyl-L-alanine methyl ester, a versatile chemical compound with significant applications in the bioscience domain, finds diverse uses across various fields. Here are the key applications of Formyl-L-alanine methyl ester presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a foundational component in peptide synthesis, Formyl-L-alanine methyl ester plays a pivotal role in constructing peptide chains. Its ester group facilitates seamless integration into peptide structures during solid-phase synthesis, a critical process for developing therapeutic peptides and investigating intricate protein-protein interactions.

Chemical Biology: Delving into chemical biology, researchers harness the potential of Formyl-L-alanine methyl ester as both a substrate and a probe. By leveraging this compound, scientists explore enzyme activities and label specific biomolecules, unraveling complex metabolic pathways and unlocking the mysteries of enzyme mechanisms at a molecular level.

Pharmaceutical Research: In the realm of drug discovery and development, Formyl-L-alanine methyl ester emerges as a valuable asset, particularly in the realm of designing enzyme inhibitors. By probing its reactivity and binding characteristics, researchers unlock the potential for generating novel compounds with therapeutic applications.

Analytical Chemistry: Within the realm of analytical chemistry, Formyl-L-alanine methyl ester finds utility in the derivation of compounds, enhancing the detection and quantification of amino acids and metabolites in samples. Employing advanced techniques such as chromatography and mass spectrometry, this compound boosts analytical sensitivity and precision in biological research and diagnostics, fostering a deeper understanding of complex biological systems.

1. Binding of indomethacin methyl ester to cyclooxygenase-2. A computational study
Menyhárt-Botond Sárosi J Mol Model. 2018 Jun 5;24(7):150. doi: 10.1007/s00894-018-3686-8.
Inhibitors selective towards the second isoform of prostaglandin synthase (cyclooxygenase, COX-2) are promising nonsteroidal anti-inflammatory drugs and antitumor medications. Methylation of the carboxylate group in the relatively nonselective COX inhibitor indomethacin confers significant COX-2 selectivity. Several other modifications converting indomethacin into a COX-2 selective inhibitor have been reported. Earlier experimental and computational studies on neutral indomethacin derivatives suggest that the methyl ester derivative likely binds to COX-2 with a similar binding mode as that observed for the parent indomethacin. However, docking studies followed by molecular dynamics simulations revealed two possible binding modes in COX-2 for indomethacin methyl ester, which differs from the experimental binding mode found for indomethacin. Both alternative binding modes might explain the observed COX-2 selectivity of indomethacin methyl ester. Graphical abstract Binding of indomethacin methyl ester to cyclooxygenase-2.
2. 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.
3. 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.
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