N-α-Carbobenzoxy-D-alanine methyl ester
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N-α-Carbobenzoxy-D-alanine methyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-001456
CAS number
67799-99-9
Molecular Formula
C12H15NO4
Molecular Weight
237.26
IUPAC Name
methyl (2R)-2-(phenylmethoxycarbonylamino)propanoate
Synonyms
Z-D-Ala-OMe
InChI
InChI=1S/C12H15NO4/c1-9(11(14)16-2)13-12(15)17-8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3,(H,13,15)/t9-/m1/s1
InChI Key
OMDVFTVXPVXANK-SECBINFHSA-N
Canonical SMILES
CC(C(=O)OC)NC(=O)OCC1=CC=CC=C1

N-α-Carbobenzoxy-D-alanine methyl ester, also recognized as Z-D-Ala-OMe, stands as a prominent chemical reagent utilized widely in biochemical research and synthetic chemistry. Below are key applications illuminated with high perplexity and burstiness:

Peptide Synthesis: Within the realm of peptide synthesis, N-α-Carbobenzoxy-D-alanine methyl ester plays a pivotal role as a protected amino acid derivative integrated into the construction of peptides. This derivative safeguards the amino acid's integrity throughout the synthesis process facilitating the creation of specific peptide sequences with precision and finesse.

Enzyme Inhibition Studies: Unveiling its versatility, this compound is a staple in investigations centered on enzyme kinetics and inhibition. It shines as a substrate analog or inhibitor in probing proteolytic enzymes shedding light on enzyme specificity and fostering the design of innovative enzyme inhibitors with potential therapeutic avenues.

Structural Biology: Foraying into structural biology, N-α-Carbobenzoxy-D-alanine methyl ester emerges as a key player serving as a precursor for crystallography endeavors. Its incorporation into peptides or proteins grants researchers insights into the atomic arrangement within these molecules a critical aspect in deciphering protein functionality and laying the groundwork for insightful drug design ventures.

Drug Development: In the dynamic landscape of drug development, this compound reigns supreme offering a valuable asset in the preliminary stages of drug discovery and screening. By tailoring the structure of N-α-Carbobenzoxy-D-alanine methyl ester medicinal chemists craft diverse small molecules for evaluation of their biological activities a pivotal step in pinpointing lead compounds for subsequent drug refinement and advancement.

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. Synthesis of New Cyclopeptide Analogues of the Miuraenamides
Sarah Kappler, Andreas Siebert, Uli Kazmaier Curr Org Synth. 2021;18(4):418-424. doi: 10.2174/1570179418666210113161550.
Introduction: Miuraenamides belong to natural marine compounds with interesting biological properties. Materials and methods: Miuraenamides initiate polymerization of monomeric actin and therefore show high cytotoxicity by influencing the cytoskeleton. New derivatives of the miuraenamides have been synthesized containing an N-methylated amide bond instead of the more easily hydrolysable ester in the natural products. Results: Incorporation of an aromatic side chain onto the C-terminal amino acid of the tripeptide fragment also led to highly active new miuraenamides. Conclusion: In this study, we showed that the ester bond of the natural product miuraenamide can be replaced by an N-methyl amide. The yields in the cyclization step were high and generally much better than with the corresponding esters. On the other hand, the biological activity of the new amide analogs was lower compared to the natural products, but the activity could significantly be increased by incorporation of a p-nitrophenyl group at the C-terminus of the peptide fragment.
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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