N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-methyl ester
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N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-methyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-003127
CAS number
45214-91-3
Molecular Formula
C11H19NO6
Molecular Weight
261.27
N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-methyl ester
IUPAC Name
(2S)-5-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid
Synonyms
Boc-Glu(OMe)-OH; (2S)-5-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid; N-Boc-L-glutamic acid 5-methyl ester; Boc-L-glutamic acid 1-methyl ester; N-Boc-glutamic acid 4-methyl ester; Boc-L-glutamic acid 5-methyl ester
Purity
≥ 95%
Density
1.182±0.060 g/cm3
Melting Point
119-123°C
Boiling Point
428.4±40.0 °C
InChI
InChI=1S/C11H19NO6/c1-11(2,3)18-10(16)12-7(9(14)15)5-6-8(13)17-4/h7H,5-6H2,1-4H3,(H,12,16)(H,14,15)/t7-/m0/s1
InChI Key
OHYMUFVCRVPMEY-ZETCQYMHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCC(=O)OC)C(=O)O

N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-methyl ester is a chemical compound often used in peptide synthesis and biochemical research. Here are some key applications for this compound:

Peptide Synthesis: This compound is commonly used as a protected amino acid in peptide synthesis, providing stability to specific amino groups during the synthesis process. Its structure allows for selective deprotection under mild conditions, making it ideal for the stepwise formation of peptides. Hence, researchers can synthesize complex peptides with high precision and reduced risk of side reactions.

Chemical Biology: In chemical biology, N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-methyl ester acts as a useful building block for the development of glutamic acid derivatives. These derivatives can be used to study protein interactions, enzyme mechanisms, and cellular processes. By integrating these compounds into biological systems, scientists can gain valuable insights into protein function and behavior.

Pharmaceutical Development: This compound plays a significant role in the development of pharmaceutical candidates, particularly in designing prodrugs. The ester moiety facilitates membrane permeability while the t-butoxycarbonyl group enhances compound stability, allowing for better pharmacokinetic profiles. This is crucial in optimizing drug delivery and efficacy for various therapeutic applications.

Bioconjugation: In the realm of bioconjugation, N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-methyl ester is employed to attach biologically active molecules to synthetic carriers. By serving as a functionalized linker, it enables the creation of hybrid molecules, such as antibody-drug conjugates or peptide-linked nanoparticles. This application is instrumental in targeted drug delivery and the development of advanced therapeutic platforms.

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