Nα-Boc-Nγ-trityl-L-asparagine
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Nα-Boc-Nγ-trityl-L-asparagine

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Category
BOC-Amino Acids
Catalog number
BAT-002962
CAS number
132388-68-2
Molecular Formula
C28H30N2O5
Molecular Weight
474.60
Nα-Boc-Nγ-trityl-L-asparagine
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-(tritylamino)butanoic acid
Synonyms
Boc-L-Asn(Trt)-OH; Nalpha-tert-Butoxycarbonyl-Ngamma-trityl-L-asparagine; (S)-2-((tert-Butoxycarbonyl)amino)-4-oxo-4-(tritylamino)butanoic acid; Boc-N-beta-Trityl-L-asparagine
Appearance
White powder
Purity
≥ 99.5% (HPLC, Chiral purity)
Density
1.202g/cm3
Melting Point
180-200 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C28H30N2O5/c1-27(2,3)35-26(34)29-23(25(32)33)19-24(31)30-28(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18,23H,19H2,1-3H3,(H,29,34)(H,30,31)(H,32,33)/t23-/m0/s1
InChI Key
PYGOCFDOBSXROC-QHCPKHFHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)NC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)O

Nα-Boc-Nγ-trityl-L-asparagine is a chemically protected form of the amino acid asparagine, commonly used in peptide synthesis and biochemical research. Here are some key applications of Nα-Boc-Nγ-trityl-L-asparagine:

Peptide Synthesis: Nα-Boc-Nγ-trityl-L-asparagine is widely used in the synthesis of peptides and proteins. Its protective groups prevent unwanted reactions at the amino and side chain amido functional groups during sequential peptide bond formation. This ensures high-yield and high-purity peptide production, facilitating research in protein function and structure.

Pharmaceutical Development: In drug development, Nα-Boc-Nγ-trityl-L-asparagine is employed for the synthesis of peptide-based therapeutics. The protected asparagine derivative allows for the construction of complex peptides with therapeutic potential, such as peptide hormones and enzyme inhibitors. Proper deprotection strategies then release the active compound, critical for studying bioactivity and therapeutic efficacy.

Structural Biology: Nα-Boc-Nγ-trityl-L-asparagine is useful in investigating protein structure and interactions. By incorporating this protected amino acid into peptide chains, researchers can study how modifications affect protein folding and stability. This is essential for understanding protein conformational changes and for designing proteins with specific properties.

Bioconjugation: This protected asparagine variant is also utilized in bioconjugation techniques to attach peptides to various biomolecules, such as antibodies and nucleic acids. The selective deprotection steps ensure that the functional group of interest is exposed for subsequent conjugation. This application is important for developing targeted drug delivery systems and diagnostic tools.

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