N-α-(t-Butoxycarbonyl)-L-glutamic acid α-phenyl ester
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N-α-(t-Butoxycarbonyl)-L-glutamic acid α-phenyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-003125
CAS number
59587-94-9
Molecular Formula
C16H21NO6
Molecular Weight
323.35
N-α-(t-Butoxycarbonyl)-L-glutamic acid α-phenyl ester
IUPAC Name
(4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-phenoxypentanoic acid
Synonyms
Boc-Glu-OPh; Boc-Glu-phenyl ester; (S)-4-[(t-Butoxycarbonyl)amino]-5-oxo-5-phenylpentanoic acid; (4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-phenoxypentanoic acid; Boc-L-glutamic acid 1-phenyl ester; L-Glutamic acid,N-((1,1-dimethylethoxy)carbonyl)-,1-phenyl ester
Purity
≥ 95%
Density
1.213±0.060 g/cm3
Boiling Point
522.1±45.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H21NO6/c1-16(2,3)23-15(21)17-12(9-10-13(18)19)14(20)22-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,18,19)/t12-/m0/s1
InChI Key
UUGORLVQLJSWBX-LBPRGKRZSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCC(=O)O)C(=O)OC1=CC=CC=C1

N-α-(t-Butoxycarbonyl)-L-glutamic acid α-phenyl ester is a chemical compound that plays a crucial role in peptide synthesis and various biochemical applications. Here are some key applications of N-α-(t-Butoxycarbonyl)-L-glutamic acid α-phenyl ester:

Peptide Synthesis: This compound is commonly used as a protected amino acid derivative in solid-phase peptide synthesis. The t-butoxycarbonyl (Boc) group serves as a temporary protective group for the amino function, preserving it during the chemical reactions that form peptide bonds. Its use facilitates the stepwise construction of peptides, crucial for producing therapeutic peptides and conducting research in protein biochemistry.

Pharmaceutical Research: N-α-(t-Butoxycarbonyl)-L-glutamic acid α-phenyl ester is involved in the synthesis of peptide-based drugs and biologically active peptides. It assists in the creation of peptide sequences that may serve as drug candidates or enzyme inhibitors. Researchers use it to design and synthesize peptides with specific biological activities and therapeutic potential.

Hydrolysis Studies: The ester linkage in this compound can be cleaved under controlled conditions, making it suitable for studying hydrolysis reactions. By analyzing the rate of hydrolysis of the ester bond, researchers can gain insights into enzyme activity and reaction mechanisms. This is valuable in enzymology and the development of hydrolytic enzyme assays.

Chemical Biology: In chemical biology, N-α-(t-Butoxycarbonyl)-L-glutamic acid α-phenyl ester is utilized as a chemical probe to study protein function and interactions. By incorporating it into peptides, scientists can create modified peptides that interact with proteins of interest to elucidate protein roles in cellular processes. This application aids in understanding protein dynamics and developing targeted therapeutics.

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