N-α-(t-Butoxycarbonyl)-L-asparagine 2-nitrophenyl ester
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N-α-(t-Butoxycarbonyl)-L-asparagine 2-nitrophenyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-003117
CAS number
38605-58-2
Molecular Formula
C15H19N3O7
Molecular Weight
353.33
N-α-(t-Butoxycarbonyl)-L-asparagine 2-nitrophenyl ester
IUPAC Name
(2-nitrophenyl) (2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
Synonyms
Boc-Asn-OPh(2-NO2); Boc-Asn-o-nitrophenyl ester; (2-nitrophenyl) (2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate; Boc-L-Asn-ONO; N-alpha-Boc-L-asparagine 2-nitrophenyl ester
Purity
98%
Storage
Store at -20 °C
InChI
InChI=1S/C15H19N3O7/c1-15(2,3)25-14(21)17-9(8-12(16)19)13(20)24-11-7-5-4-6-10(11)18(22)23/h4-7,9H,8H2,1-3H3,(H2,16,19)(H,17,21)/t9-/m0/s1
InChI Key
KSOSHRILCLONAA-VIFPVBQESA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)N)C(=O)OC1=CC=CC=C1[N+](=O)[O-]

N-α-(t-Butoxycarbonyl)-L-asparagine 2-nitrophenyl ester is a specialized reagent widely utilized in peptide synthesis and various biochemical applications. Here are the key applications of this compound presented with high perplexity and burstiness:

Peptide Synthesis: Acting as a shielded amino acid derivative in solid-phase peptide synthesis, this compound bears the crucial Boc (t-Butoxycarbonyl) moiety that safeguards the amine functionality of asparagine throughout peptide chain extension. Subsequently, this protective group is cleaved to enable peptide bond formation, ensuring the precise alignment of desired peptide sequences.

Enzyme Mechanism Studies: In the realm of enzyme mechanism exploration, N-α-(t-Butoxycarbonyl)-L-asparagine 2-nitrophenyl ester emerges as a pivotal tool, particularly in investigations involving proteases. Serving as a mimetic substrate, it assists researchers in unraveling intricate enzyme-substrate interactions and catalytic mechanisms. This aids in gaining profound insights into enzyme specificity and potential tactics for inhibition.

Chemical Biology: Within the sphere of chemical biology research, this compound finds utility in crafting chemically altered peptides for the investigation of protein-protein interactions. Through its incorporation into peptide structures, scientists can introduce targeted modifications that facilitate the detection or isolation of protein complexes, pivotal for comprehending intricate cellular signaling pathways and molecular interactions.

Drug Development: Furthermore, this reagent proves invaluable in the advancement of peptide-based therapeutics. By enabling precise amino acid modifications and protection, it streamlines the creation of peptide drugs with heightened stability and bioavailability. This innovative approach holds promise for the development of novel treatments spanning infectious diseases to cancer, pushing the boundaries of therapeutic innovation.

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