Nα-Z-Nβ-xanthyl-D-asparagine
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Nα-Z-Nβ-xanthyl-D-asparagine

* 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-001443
CAS number
1313054-82-8
Molecular Formula
C25H22N2O6
Molecular Weight
446.50
IUPAC Name
(2R)-4-oxo-2-(phenylmethoxycarbonylamino)-4-(9H-xanthen-9-ylamino)butanoic acid
Synonyms
Z-D-Asn(Xan)-OH; Na-Z-Nss-xanthyl-D-asparagine; (R)-4-((9H-Xanthen-9-yl)amino)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid; Nalpha-Z-Nbeta-xanthyl-D-asparagine
Appearance
White powder
Purity
≥ 99% (HPLC)
Melting Point
181-187°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C25H22N2O6/c28-22(14-19(24(29)30)26-25(31)32-15-16-8-2-1-3-9-16)27-23-17-10-4-6-12-20(17)33-21-13-7-5-11-18(21)23/h1-13,19,23H,14-15H2,(H,26,31)(H,27,28)(H,29,30)/t19-/m1/s1
InChI Key
UCGUJYWDGWXJFG-LJQANCHMSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NC(CC(=O)NC2C3=CC=CC=C3OC4=CC=CC=C24)C(=O)O

Nα-Z-Nβ-xanthyl-D-asparagine is a protected amino acid derivative commonly used in peptide synthesis. The "Z" group (benzyloxycarbonyl) protects the N-terminal amine, while the xanthyl group protects the side chain amine of asparagine. This dual protection is essential to prevent undesired side reactions during peptide bond formation, ensuring the synthesis proceeds efficiently. D-asparagine is the D-enantiomer of the naturally occurring L-asparagine, often used in specialized applications where chirality is critical.

One of the primary industrial applications of Nα-Z-Nβ-xanthyl-D-asparagine is in pharmaceutical peptide synthesis. Protected amino acids like this are crucial for building complex peptide drugs, which are used in treatments for diseases such as cancer, diabetes, and infectious diseases. The high specificity of peptide drugs makes them valuable in targeted therapies, ensuring fewer side effects compared to small-molecule drugs.

Another significant application is in the production of diagnostic peptides. These peptides are used in diagnostic assays, where their ability to bind specific biological targets is leveraged to detect diseases or monitor therapeutic responses. Nα-Z-Nβ-xanthyl-D-asparagine ensures that the peptides can be synthesized with the necessary purity and stability for sensitive diagnostic applications.

In addition to pharmaceuticals and diagnostics, this compound is used in the food and cosmetic industries. In food science, peptides with specific biological activities are incorporated into products to enhance nutritional or health benefits. Similarly, in cosmetics, peptides are added to formulations for their anti-aging or skin-repairing properties, making Nα-Z-Nβ-xanthyl-D-asparagine a key player in these formulations.

Lastly, Nα-Z-Nβ-xanthyl-D-asparagine is used in academic and industrial research. Researchers studying protein-protein interactions or enzymatic processes often require well-defined peptides for their experiments. This compound helps in generating high-quality peptides, contributing to advancements in biochemical research.

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