Nα-Z-L-asparagine methyl ester
Need Assistance?
  • US & Canada:
    +
  • UK: +

Nα-Z-L-asparagine methyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
CBZ-Amino Acids
Catalog number
BAT-003222
CAS number
4668-37-5
Molecular Formula
C13H16N2O5
Molecular Weight
280.28
Nα-Z-L-asparagine methyl ester
IUPAC Name
methyl (2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoate
Synonyms
Z-L-Asn-Ome; Methyl N~2~-[(Benzyloxy)Carbonyl]-L-Asparaginate
Appearance
White powder
Purity
≥ 98% (HPLC)
Melting Point
130-135 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H16N2O5/c1-19-12(17)10(7-11(14)16)15-13(18)20-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3,(H2,14,16)(H,15,18)/t10-/m0/s1
InChI Key
CQIPRSHYISKHFR-JTQLQIEISA-N
Canonical SMILES
COC(=O)C(CC(=O)N)NC(=O)OCC1=CC=CC=C1

Nα-Z-L-asparagine methyl ester, a versatile chemical compound, finds applications in pharmaceuticals, biochemistry, and synthetic chemistry. Here are the key applications:

Peptide Synthesis: Widely employed as a critical building block in peptide and protein synthesis, Nα-Z-L-asparagine methyl ester plays a pivotal role. The presence of its protected amine group (Nα-Z) facilitates seamless integration into peptide chains, avoiding undesirable side reactions. Its utility as an essential intermediate enables the creation of bioactive peptides, crucial for both research and therapeutic endeavors.

Drug Development: At the forefront of pharmaceutical innovation, Nα-Z-L-asparagine methyl ester is a strategic tool for crafting novel therapeutic agents. Through structural modifications, researchers can generate derivatives with diverse pharmacological activities. These derivatives undergo rigorous screening against various disease targets, aiding in the ongoing quest for groundbreaking pharmaceutical discoveries.

Enzyme Studies: Serving as a versatile substrate or inhibitor in biochemical examinations of enzymes, Nα-Z-L-asparagine methyl ester plays a vital role. Interactions with specific enzymes offer insights into their catalytic mechanisms and substrate preferences. This knowledge is instrumental in deciphering enzyme functionality and in designing targeted enzyme inhibitors tailored for therapeutic applications.

Industrial Biotechnology: In the dynamic realm of industrial biotechnology, Nα-Z-L-asparagine methyl ester emerges as a key starting material for producing a myriad of biochemicals. Its integration into fermentation or enzymatic processes fosters the synthesis of valuable compounds such as bioactive peptides and amino acids. This application not only supports the development of efficient bioprocesses but also contributes to sustainable industrial practices.

1. Alginate ester: New moisture-scavenging excipients for direct compressible pharmaceutical tableting
Noelia M Sanchez-Ballester, Philippe Trens, Jean-Christophe Rossi, Ian Soulairol Carbohydr Polym. 2022 Dec 1;297:120063. doi: 10.1016/j.carbpol.2022.120063. Epub 2022 Aug 31.
The objective of this work is to evaluate methyl ester alginates and alginic acid (AA) as moisture-scavenging excipients for the formulation of aspirin tablets obtained by direct compression. The tablets were stored at accelerated conditions (40 °C/75 % RH) and assessed for changes in tensile strength, mass, thickness and disintegration time. While moisture caused a reduction in the hardness of MCC and AA tablets, hardness of the tablets made from methylated materials was virtually unaffected. The physical stability of alginate ester tablets was found to be related to their increased plastic deformation leading to extended interparticle contact with less impact on tablet porosity. Finally, the combination of higher moisture affinity and lower water dissociation exhibited by alginates esters resulted in tablets with the lowest aspirin degradation. These findings suggest that excipients with high water retention can act as moisture-scavengers without losing their functional properties and reducing the degradation of moisture-sensitive drugs.
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. 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.
Online Inquiry
Verification code
Inquiry Basket