N-α-Carbobenzoxy-β-chloro-L-alanine methyl ester
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N-α-Carbobenzoxy-β-chloro-L-alanine methyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-006934
CAS number
62107-38-4
Molecular Formula
C12H14ClNO4
Molecular Weight
271.70
N-α-Carbobenzoxy-β-chloro-L-alanine methyl ester
IUPAC Name
methyl (2R)-3-chloro-2-(phenylmethoxycarbonylamino)propanoate
Synonyms
Z-Ala(3-Cl)-OMe; Z-Ala(β-Cl)-OMe; N-α-Carbobenzoxy-3-chloro-L-alanine methyl ester
Appearance
White to Off-White Solid
Purity
98%
Density
1.258±0.06 g/cm3(Predicted)
Melting Point
54.2-54.9 °C
Boiling Point
411.3±45.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C12H14ClNO4/c1-17-11(15)10(7-13)14-12(16)18-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3,(H,14,16)/t10-/m0/s1
InChI Key
UQUQXYVMAKOZMV-JTQLQIEISA-N
Canonical SMILES
COC(=O)C(CCl)NC(=O)OCC1=CC=CC=C1

N-α-Carbobenzoxy-β-chloro-L-alanine methyl ester, a synthetic compound with specialized applications in biochemical and pharmaceutical, research offers a myriad of possibilities for cutting-edge innovation. Here we explore key applications with a high degree of perplexity and burstiness:

Peptide Synthesis: A cornerstone in the realm of biochemistry, N-α-Carbobenzoxy-β-chloro-L-alanine methyl ester serves as a fundamental building block in the intricate synthesis of complex peptides. Acting as a shielded amino acid it seamlessly integrates into peptide chains avoiding undesirable side reactions. This precision enables the creation of peptides with tailored sequences and modifications catering to both research and therapeutic endeavors with unparalleled specificity and finesse.

Enzyme Inhibition Studies: Delving into the depths of enzymology, this compound proves invaluable for unraveling the mysteries of enzyme inhibition particularly in the context of chlorinated amino acid derivatives. Researchers harness its properties to illuminate the intricate dance between enzymes and substrates paving the way for the development of potential inhibitors targeting therapeutic endpoints. These endeavors hold the promise of unearthing novel drugs that finely modulate enzyme activity ushering in a new era of pharmaceutical breakthroughs.

Drug Development: Positioned at the forefront of pharmaceutical exploration N-α-Carbobenzoxy-β-chloro-L-alanine methyl ester emerges as a pivotal precursor in the synthesis of bioactive compounds. Its distinctive chemical architecture lends itself to transformation into a diverse array of derivatives acting as the springboard for innovative drug discovery efforts. This transformative ability facilitates the identification of novel therapeutic agents boasting enhanced efficacy and safety profiles reshaping the landscape of medicinal advancements.

Structural Biology: Embarking on a journey through the intricate world of proteins and peptides, N-α-Carbobenzoxy-β-chloro-L-alanine methyl ester plays a vital role in unraveling the mysteries of structural biology. Through its incorporation into protein sequences researchers embark on a quest to unravel the enigma of protein folding stability and function. The insights gleaned from these studies not only deepen our understanding of protein dynamics but also lay the groundwork for the design of groundbreaking biomolecules pushing the boundaries of structural analysis to unprecedented heights.

1. 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.
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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