N-β-(t-Butoxycarbonyl)-L-β-homoasparagine
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N-β-(t-Butoxycarbonyl)-L-β-homoasparagine

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Category
BOC-Amino Acids
Catalog number
BAT-005174
CAS number
336182-03-7
Molecular Formula
C10H18N2O5
Molecular Weight
246.27
N-β-(t-Butoxycarbonyl)-L-β-homoasparagine
IUPAC Name
(3S)-5-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid
Synonyms
Boc-Asn-(C#CH2)OH; Boc-β-homoAsn-OH; (S)-3-[(t-Butoxycarbonyl)amino]-5-amino-5-oxopentanoic acid; (S)-3-(Boc-amino)-4-carbamoylbutyric acid; (S)-5-Amino-3-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid; BOC-L-β-HOMOASPARAGINE; Boc-L-β-homoasparagine; (S)-3-(Boc-amino)-4-carbamoylbutyric acid
Appearance
White to off-white solid
Purity
≥ 99% (NMR)
Density
1.220±0.060 g/cm3
Boiling Point
506.9±45.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H18N2O5/c1-10(2,3)17-9(16)12-6(4-7(11)13)5-8(14)15/h6H,4-5H2,1-3H3,(H2,11,13)(H,12,16)(H,14,15)/t6-/m0/s1
InChI Key
IUNRBHPDQJCDLT-LURJTMIESA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)N)CC(=O)O

N-β-(t-Butoxycarbonyl)-L-β-homoasparagine, a derivative amino acid with a protective function, finds diverse applications in peptide synthesis and pharmaceutical research.

Peptide Synthesis: Widely employed in peptide and protein synthesis, this compound acts as a foundational component for constructing peptide chains. The t-Butoxycarbonyl (Boc) group shields the amino functionality, enabling sequential peptide bond formation devoid of undesired side reactions. Upon completion of peptide synthesis, the Boc group can be effortlessly eliminated under acidic conditions, yielding the final product.

Drug Development: In the realm of pharmaceuticals, N-β-(t-Butoxycarbonyl)-L-β-homoasparagine plays a pivotal role in crafting peptide-based drugs. Peptides synthesized using this compound can be tailored to target specific disease pathways, driving the creation of innovative therapeutics. This customization facilitates the generation of highly specific and potent drug candidates with minimal adverse effects.

Enzyme Studies: Utilized in investigating enzyme-substrate interactions and enzyme kinetics, this compound aids in understanding how enzymes recognize and process substrates. By integrating N-β-(t-Butoxycarbonyl)-L-β-homoasparagine into substrate analogs, researchers explore enzyme mechanisms crucial for designing enzyme inhibitors and activators.

Bioconjugation: In the realm of bioconjugate chemistry, this protected amino acid serves to link peptides to diverse molecules such as drugs, labels, or polymers. The Boc group ensures the amino acid’s reactivity and specificity for conjugation reactions. This application is particularly valuable for creating targeted drug delivery systems and diagnostic tools, enhancing the precision and efficacy of medical interventions.

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