Boc-L-glutamic acid-α-benzyl ester
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Boc-L-glutamic acid-α-benzyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-004539
CAS number
30924-93-7
Molecular Formula
C17H23NO6
Molecular Weight
337.40
Boc-L-glutamic acid-α-benzyl ester
IUPAC Name
(4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-phenylmethoxypentanoic acid
Synonyms
Boc-L-Glu-Obzl; tert-Butyloxycarbonyl-glutamic acid 1-benzyl ester
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.197g/cm3
Melting Point
88-98 °C
Boiling Point
522.6±50.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C17H23NO6/c1-17(2,3)24-16(22)18-13(9-10-14(19)20)15(21)23-11-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H,18,22)(H,19,20)/t13-/m0/s1
InChI Key
CVZUKWBYQQYBTF-ZDUSSCGKSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCC(=O)O)C(=O)OCC1=CC=CC=C1

Boc-L-glutamic acid-α-benzyl ester is a chemical compound pivotal in peptide synthesis and pharmaceutical investigation:

Peptide Synthesis: A fundamental component in solid-phase peptide synthesis (SPPS), Boc-L-glutamic acid-α-benzyl ester serves as a shielded amino acid, with the Boc (tert-butoxycarbonyl) group safeguarding the amino function from undesired side reactions during peptide elongation. Post-synthesis, acidic conditions can strip the Boc group, unveiling the desired peptide structure with precision and finesse.

Drug Development: Within peptide-based drug research, this compound acts as a crucial intermediate, enabling researchers to modulate the lipophilicity and membrane permeability of peptides by its incorporation. This modification can enhance oral bioavailability, paving the way for the design of innovative therapeutic agents boasting superior pharmacokinetic properties.

Bioconjugation: In the realm of bioconjugation, Boc-L-glutamic acid-α-benzyl ester plays a key role in linking peptides or biomolecules to carrier systems like nanoparticles or polymers. This linkage facilitates targeted drug delivery mechanisms and controlled release of therapeutic agents, thereby advancing drug delivery technologies with finesse and precision.

Structural Studies: Vital for structural biology, this compound aids in the preparation of modified peptides essential for NMR or crystallography investigations. By introducing ester-linked amino acids, scientists can unravel the structural and functional implications of such modifications, offering insights into protein folding, stability, and interactions crucial for designing stable and functional peptide structures with meticulous attention to detail.

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