4-Benzyl N-(tert-butoxycarbonyl)-L-aspartate
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4-Benzyl N-(tert-butoxycarbonyl)-L-aspartate

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Category
BOC-Amino Acids
Catalog number
BAT-002756
CAS number
7536-58-5
Molecular Formula
C16H21NO6
Molecular Weight
323.30
4-Benzyl N-(tert-butoxycarbonyl)-L-aspartate
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-phenylmethoxybutanoic acid
Synonyms
Boc-L-Asp(OBzl)-OH; (S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid
Appearance
White or off-white powder
Purity
≥ 98.5% (HPLC)
Density
1.1728 g/cm3(rough estimate)
Melting Point
96-105 °C
Boiling Point
461.82°C (rough estimate)
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H21NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-13(18)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1
InChI Key
SOHLZANWVLCPHK-LBPRGKRZSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)OCC1=CC=CC=C1)C(=O)O

4-Benzyl N-(tert-butoxycarbonyl)-L-aspartate, a chemically synthesized compound with diverse applications in bioscience, serves as a fundamental building block in multiple domains. Here are four key applications of this compound:

Peptide Synthesis: Central to peptide synthesis, 4-Benzyl N-(tert-butoxycarbonyl)-L-aspartate acts as a crucial protective agent during amino acid assembly, ensuring precise deprotection and coupling steps in chemical reactions. This meticulous process is essential for crafting specific peptide sequences with exceptional purity and yield, driving advancements in peptide biology and beyond.

Drug Development: In the realm of pharmaceutical exploration, this compound facilitates the synthesis of peptide-based therapeutics, enabling the creation of novel drugs targeted at diverse diseases. By leveraging solid-phase peptide synthesis methods, researchers can develop peptides that function as potent enzyme inhibitors, hormones, or prospective vaccine components.

Enzyme Substrate Studies: A key player in investigating enzymatic behavior and substrate selectivity, 4-Benzyl N-(tert-butoxycarbonyl)-L-aspartate is integrated into substrate analogs to probe the intricate interactions between enzymes and their substrates. This exploration is critical for deciphering enzyme mechanisms and designing effective enzyme inhibitors, shedding light on the molecular intricacies of biological processes.

Structural Biology: Engaging in structural biology inquiries, this compound aids in the analysis of modified peptides to unravel their complex three-dimensional configurations. Employing techniques like X-ray crystallography and nuclear magnetic resonance (NMR) spectroscopy, researchers dissect the structural nuances essential for understanding protein functions and interactions. This profound comprehension underpins advancements in drug development and diverse bioscience applications.

1.Erratum: (4Z)-4-Benzyl-idene-2-phenyl-1,3-oxazol-5(4H)-one. Corrigendum.
Asiri AM1, Faidallah HM2, Sobahi TR2, Ng SW3, Tiekink ER4. Acta Crystallogr E Crystallogr Commun. 2015 Oct 17;71(Pt 11):e4. doi: 10.1107/S2056989015019271. eCollection 2015.
In the paper by Asiri et al. [Acta Cryst. (2012), E68, o1154], the title and the chemical name of one of the reagents used in the synthesis are corrected.[This corrects the article DOI: 10.1107/S1600536812011579.].
2.Design and synthesis of 4-benzyl-1-(2H)-phthalazinone derivatives as novel androgen receptor antagonists.
Inoue K1, Urushibara K1, Kanai M1, Yura K2, Fujii S3, Ishigami-Yuasa M4, Hashimoto Y5, Mori S4, Kawachi E4, Matsumura M1, Hirano T4, Kagechika H4, Tanatani A6. Eur J Med Chem. 2015 Sep 18;102:310-9. doi: 10.1016/j.ejmech.2015.08.002. Epub 2015 Aug 6.
The androgen receptor (AR) plays important roles in multiple physiological functions, including differentiation, growth, and maintenance of male reproductive organs, and also has effects on hair and skin. In this paper, we report the synthesis of nonsteroidal AR antagonists having a 4-benzyl-1-(2H)-phthalazinone skeleton. Among the synthesized compounds, 11c with two ortho-substituents on the phenyl group potently inhibited SC-3 cell proliferation (IC50: 0.18 μM) and showed high wt AR-binding affinity (IC50: 10.9 μM), comparable to that of hydroxyflutamide (3). Compound 11c also inhibited proliferation of LNCaP cells containing T877A-mutated AR. Docking study of 11c with the AR ligand-binding domain indicated that the benzyl group is important for the antagonism. These phthalazinone derivatives may be useful for investigating potential clinical applications of AR antagonists.
3.Crystal structure of 4-benzyl-2H-benzo[b][1,4]thia-zin-3(4H)-one.
Sebbar NK1, Ellouz M1, Essassi EM1, Ouzidan Y2, Mague JT3. Acta Crystallogr E Crystallogr Commun. 2015 Nov 28;71(Pt 12):o999. doi: 10.1107/S2056989015022276. eCollection 2015.
In the title compound, C15H13NOS, the thia-zine ring adopts a twisted boat conformation and the dihedral angle between the aromatic rings is 86.54 (4)°. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, resulting in chains along [010].
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