Fmoc-L-alanine methyl ester
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Fmoc-L-alanine methyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-001986
CAS number
146346-88-5
Molecular Formula
C19H19NO4
Molecular Weight
325.33
IUPAC Name
methyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
Synonyms
Fmoc-L-Ala-Ome; methyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
Appearance
White powder
Purity
≥ 99% (HPLC)
Melting Point
113-119°C
Boiling Point
497.3±28.0°C at 760 mmHg
Storage
Store at RT
InChI
InChI=1S/C19H19NO4/c1-12(18(21)23-2)20-19(22)24-11-17-15-9-5-3-7-13(15)14-8-4-6-10-16(14)17/h3-10,12,17H,11H2,1-2H3,(H,20,22)/t12-/m0/s1
InChI Key
NLYFFHNUTFDXLO-LBPRGKRZSA-N
Canonical SMILES
CC(C(=O)OC)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-L-alanine methyl ester, a derivative of protected amino acid, serves as a cornerstone in peptide synthesis and research. Here are the key applications of this compound, presented with a high degree of perplexity and burstiness:

Solid-Phase Peptide Synthesis: In the intricate world of peptide synthesis, Fmoc-L-alanine methyl ester plays a pivotal role as a fundamental building block. The Fmoc group elegantly shields the amino group throughout the synthesis process, allowing for meticulous and sequential addition of amino acids. This method, essential for crafting peptides of exceptional purity and customized sequences, stands as a linchpin in both research and therapeutic endeavors.

Drug Development: At the forefront of pharmaceutical innovation, Fmoc-L-alanine methyl ester emerges as a key player in the design and synthesis of peptide-based drug candidates. By harnessing this derivative, researchers can engineer peptides with precise sequences tailored to target disease-associated proteins or pathways. This strategic approach propels the discovery of novel drugs boasting enhanced efficacy and minimized side effects, reshaping the landscape of therapeutic interventions.

Biochemical Studies: Delving into the realm of biochemical research, Fmoc-L-alanine methyl ester emerges as a vital tool for unraveling protein interactions and enzyme mechanisms. By integrating this derivative into synthetic peptides, scientists can probe the intricate dance between peptides and biological molecules like proteins and enzymes. This in-depth understanding of protein functionality serves as a cornerstone for developing potent enzyme inhibitors or activators, shedding light on the intricate machinery governing biological processes.

Material Science: Beyond the realms of biology, Fmoc-L-alanine methyl ester finds its utility in the realm of material science, driving innovations in biomaterials and nanomaterials. By infusing this amino acid derivative into polymer matrices, researchers engineer materials endowed with tailored properties such as augmented mechanical strength or biocompatibility. These advanced materials hold promise in diverse applications spanning tissue engineering, drug delivery systems, and other burgeoning fields of biomedicine, heralding a new era of material innovation.

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. Efficient Fmoc-Protected Amino Ester Hydrolysis Using Green Calcium(II) Iodide as a Protective Agent
Renaud Binette, Michael Desgagné, Camille Theaud, Pierre-Luc Boudreault Molecules. 2022 Apr 27;27(9):2788. doi: 10.3390/molecules27092788.
In order to modify amino acids, the C-terminus carboxylic acid usually needs to be protected, typically as a methyl ester. However, standard cleavage of methyl esters requires either highly basic or acidic conditions, which are not compatible with Fmoc or acid-labile protecting groups. This highlights the need for orthogonal conditions that permit selective deprotection of esters to create SPPS-ready amino acids. Herein, mild orthogonal ester hydrolysis conditions are systematically explored using calcium(II) iodide as a protective agent for the Fmoc protecting group and optimized for a broad scope of amino esters. Our optimized reaction improved on the already known trimethyltin hydroxide, as it produced better yields with greener, inexpensive chemicals and a less extensive energy expenditure.
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