N-α-(t-Butoxycarbonyl)-D-glutamic acid γ-benzyl ester
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N-α-(t-Butoxycarbonyl)-D-glutamic acid γ-benzyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-003098
CAS number
35793-73-8
Molecular Formula
C17H23NO6
Molecular Weight
337.36
N-α-(t-Butoxycarbonyl)-D-glutamic acid γ-benzyl ester
IUPAC Name
(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-phenylmethoxypentanoic acid
Synonyms
Boc-D-Glu(OBzl)-OH; (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-phenylmethoxypentanoic acid; N-tert-Butoxycarbonyl-D-glutamic acid 5-benzyl ester; Boc-D-Glutamic acid 5-benzylester
Purity
≥ 95%
Density
1.197 g/cm3
Melting Point
69-71 °C
Boiling Point
522.6±50.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C17H23NO6/c1-17(2,3)24-16(22)18-13(15(20)21)9-10-14(19)23-11-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H,18,22)(H,20,21)/t13-/m1/s1
InChI Key
AJDUMMXHVCMISJ-CYBMUJFWSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCC(=O)OCC1=CC=CC=C1)C(=O)O

N-α-(t-Butoxycarbonyl)-D-glutamic acid γ-benzyl ester, a versatile chemical compound, finds extensive use in organic synthesis and pharmacology. Here are four key applications of N-α-(t-Butoxycarbonyl)-D-glutamic acid γ-benzyl ester:

Peptide Synthesis: Playing a pivotal role in peptide synthesis, this compound acts as a protected amino acid derivative, aiding in the construction of intricate peptides and proteins. The t-Butoxycarbonyl (Boc) group shields the amino group, while the γ-benzyl ester safeguards the carboxyl group during synthesis. These protective measures are essential for achieving selective reactions and maintaining high purity in peptide assembly.

Pharmaceutical Research: In the realm of drug development, this compound serves as an intermediate in synthesizing peptide-based drugs, including enzyme inhibitors and therapeutic peptides. Its Boc-protection permits controlled deprotection and coupling reactions, facilitating the creation of bioactive compounds. Researchers can systematically introduce modifications to enhance drug properties, such as potency and selectivity, driving progress in pharmaceutical research.

Chemical Biology: N-α-(t-Butoxycarbonyl)-D-glutamic acid γ-benzyl ester plays a crucial role in studying protein-ligand interactions and enzyme mechanisms. By integrating protected amino acids into specific protein sequences, researchers can investigate binding sites and catalytic residues, gaining insights into enzyme function. This method aids in designing inhibitors or activators, shedding light on intricate biochemical processes.

Materials Science: This compound is instrumental in developing novel materials, especially in polymer science. It allows for the incorporation of functional groups into polymer chains, influencing the properties of the material. Such modifications are indispensable for crafting advanced materials with specific characteristics, suitable for diverse applications, including drug delivery systems and biocompatible surfaces.

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