Fmoc-L-glutamic acid γ-allyl ester
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Fmoc-L-glutamic acid γ-allyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-003756
CAS number
133464-46-7
Molecular Formula
C23H23NO6
Molecular Weight
409.42
Fmoc-L-glutamic acid γ-allyl ester
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid
Synonyms
Fmoc-L-Glu(OAll)-OH; Fmoc-L-glutamic acid 5-allyl ester; 5-Allyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamate; N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamic Acid 5-Allyl Ester; (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid; 5-Allyl N-Fmoc-L-glutamate
Appearance
White powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.264±0.06 g/cm3
Melting Point
120-135 °C
Boiling Point
650.1±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C23H23NO6/c1-2-13-29-21(25)12-11-20(22(26)27)24-23(28)30-14-19-17-9-5-3-7-15(17)16-8-4-6-10-18(16)19/h2-10,19-20H,1,11-14H2,(H,24,28)(H,26,27)/t20-/m0/s1
InChI Key
LRBARFFNYOKIAX-FQEVSTJZSA-N
Canonical SMILES
C=CCOC(=O)CCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-L-glutamic acid γ-allyl ester, a versatile chemical compound widely utilized in peptide synthesis and biochemical research, offers a plethora of applications.

Peptide Synthesis: In the intricate realm of peptide synthesis, Fmoc-L-glutamic acid γ-allyl ester emerges as a foundational and versatile component for constructing elaborate peptide sequences. Its protective Fmoc shielding safeguards the amino group during synthesis, facilitating the sequential addition of amino acids. By selectively removing the γ-allyl ester moiety, possibilities arise for side chain modifications or further reactions, enriching the versatility and intricacy of peptide assembly.

Bioconjugation: Serving as a linchpin in bioconjugation methodologies, this compound is pivotal for linking peptides to a diverse array of molecules, ranging from proteins to polymers for various applications. The reactive allyl ester functionality acts as a beacon for chemical modifications, enabling the creation of multifunctional bioconjugates. These bioconjugates find utility in drug delivery systems, diagnostics, and therapeutic exploration, highlighting the adaptability and versatility of this compound.

Structural Biology: Within the domain of structural biology, Fmoc-L-glutamic acid γ-allyl ester assumes a critical role in synthesizing peptides tailored for crystallization studies. By incorporating this compound into peptides, researchers can introduce specific modifications that promote crystal growth or stabilize structures, enhancing the quality of X-ray crystallographic data. This heightened precision aids in the more accurate determination of three-dimensional protein structures, unveiling insights into the intricate world of molecular architecture.

Drug Development: Positioned at the forefront of drug development, Fmoc-L-glutamic acid γ-allyl ester plays a pivotal role in shaping peptide-based drug candidates with optimized properties. Acting as a scaffold for fine-tuning peptide sequences to enhance stability, bioavailability, and target specificity, this compound enables the engineering of peptides with augmented therapeutic potential across a spectrum of diseases. Through strategic modification of the γ-allyl ester, researchers unlock new possibilities in pharmacology, ushering in innovative approaches in drug development.

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