Nα-Boc-D-asparagine
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Nα-Boc-D-asparagine

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Nα-Boc-D-asparagine is an N-Boc-protected form of D-Asparagine. D-Asparagine is an isomer of L-Asparagine and is used by bacteria (such as Saccharomyces cerevisiae) as a sole nitrogen source for replication. L-Asparagine is also a competitive inhibitor of staphylococcal L-asparaginase and is used as a reagent to synthesize peptide antibiotics.

Category
BOC-Amino Acids
Catalog number
BAT-002938
CAS number
75647-01-7
Molecular Formula
C9H16N2O5
Molecular Weight
232.20
Nα-Boc-D-asparagine
IUPAC Name
(2R)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid
Synonyms
Boc-D-Asn-OH; Boc-(R)-2-aminosuccinic acid 4-amide monohydrate; (2R)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid; Nalpha-Boc-D-asparagine; Boc-L-Asn-OH; Boc-D-asparagine; BOC-D-ASN
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.253 g/cm3
Melting Point
175-181 °C
Boiling Point
481.7 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H16N2O5/c1-9(2,3)16-8(15)11-5(7(13)14)4-6(10)12/h5H,4H2,1-3H3,(H2,10,12)(H,11,15)(H,13,14)/t5-/m1/s1
InChI Key
FYYSQDHBALBGHX-RXMQYKEDSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)N)C(=O)O

Nα-Boc-D-asparagine, a protected amino acid derivative widely utilized in peptide synthesis, serves as a fundamental component in diverse applications. Here are the key applications intricately presented with high perplexity and burstiness:

Peptide Synthesis: Acting as a pivotal building block in peptide and protein synthesis, Nα-Boc-D-asparagine plays a crucial role in ensuring the seamless construction of complex molecular structures. The Boc (tert-butyloxycarbonyl) group serves to safeguard the amino group during the elongation process, effectively preventing undesired side reactions. This precise technique guarantees the accurate assembly of peptides with intricate sequences, fostering breakthroughs in the realm of molecular design.

Pharmaceutical Research: At the forefront of drug development, Nα-Boc-D-asparagine embodies a key player in the creation and synthesis of peptide-based pharmaceuticals. These specialized drugs, often mimicking natural peptides, boast remarkable specificity and potency against their intended targets. The integration of Nα-Boc-D-asparagine facilitates the production of stable bioactive compounds, driving forward the essential work conducted in the realm of therapeutic research.

Bioconjugation: In the field of bioconjugation, Nα-Boc-D-asparagine takes center stage in linking peptides to various molecules, including drugs, polymers, and nanoparticles. This intricate process elevates the properties of the resulting conjugates, enhancing their stability, solubility, and targeting capabilities. These bioconjugates serve as indispensable tools in targeted drug delivery and imaging applications, pushing the boundaries of precision medicine and molecular diagnostics.

Structural Biology: Enabling the incorporation of non-standard amino acids into peptides and proteins, Nα-Boc-D-asparagine plays a pivotal role in advancing structural biology research. By leveraging modified peptides, researchers gain valuable insights into the intricate interplay of specific residues in protein folding and stability. This deep understanding of protein biophysics and dynamics contributes to a comprehensive comprehension of molecular structures and functions, shedding light on the complexities of biological systems.

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