Nα-Z-L-asparagine
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Nα-Z-L-asparagine

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A Cbz-protected L-asparagine, which is a non-essential amino acid in humans, promoting cancer cell proliferation.

Category
CBZ-Amino Acids
Catalog number
BAT-000461
CAS number
2304-96-3
Molecular Formula
C12H14N2O5
Molecular Weight
266.30
Nα-Z-L-asparagine
IUPAC Name
(2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid
Synonyms
Z-L-Asn-OH; N-Cbz-L-asparagine; Cbz-Asn-OH; (S)-2-Benzyloxycarbonylamino-succinamic acid
Appearance
White to off-white powder
Purity
≥ 99 % (HPLC)
Density
1.355 g/cm3
Melting Point
155-172 °C
Boiling Point
580.6 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C12H14N2O5/c13-10(15)6-9(11(16)17)14-12(18)19-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,13,15)(H,14,18)(H,16,17)/t9-/m0/s1
InChI Key
FUCKRCGERFLLHP-VIFPVBQESA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NC(CC(=O)N)C(=O)O

Nα-Z-L-asparagine, a derivative of the amino acid asparagine adorned with a benzyloxycarbonyl (Z) protecting group, boasts various applications in bioscience. Here we explore the key applications of Nα-Z-L-asparagine:

Peptide Synthesis: Widely utilized in peptide and protein synthesis, Nα-Z-L-asparagine plays a pivotal role. The Z-protecting group shields the amino group during peptide coupling, ensuring specific reactions. This precision enables the construction of intricate peptide sequences with exceptional accuracy and purity.

Enzyme Inhibition Studies: In the realm of enzyme analysis, Nα-Z-L-asparagine emerges as a valuable tool for exploring enzymes that target asparagine or its counterparts. Through the use of this modified asparagine derivative, scientists can delve into enzyme specificity and catalytic mechanisms. These insights pave the way for novel enzyme inhibitors with therapeutic or industrial applications.

Structural Biology: Within structural biology, Nα-Z-L-asparagine finds utility as a foundational unit for crafting labeled peptides or proteins crucial for crystallization or NMR studies. The presence of the Z-protecting group bolsters the stability and solubility of peptides throughout purification and crystallization, facilitating the acquisition of top-tier structural data for biological macromolecules.

Drug Development: Positioned as a key intermediate in pharmaceutical synthesis, Nα-Z-L-asparagine stands at the forefront of drug development endeavors. Its structural adaptability allows for tailored modifications, yielding compounds with therapeutic potential. By strategically incorporating Nα-Z-L-asparagine into drug candidates, medicinal chemists can optimize pharmacological properties, enhancing efficacy and safety profiles.

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