Fmoc-D-glutamic acid γ-allyl ester
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Fmoc-D-glutamic acid γ-allyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-003637
CAS number
204251-33-2
Molecular Formula
C23H23NO6
Molecular Weight
409.40
Fmoc-D-glutamic acid γ-allyl ester
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid
Synonyms
Fmoc-D-Glu(OAll)-OH; Fmoc-D-glutamic acid 5-allyl ester; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)-amino)-5-(allyloxy)-5-oxopentanoic acid
Appearance
White powder
Purity
≥ 99.7% (HPLC, Chiral purity)
Melting Point
121-131 °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-/m1/s1
InChI Key
LRBARFFNYOKIAX-HXUWFJFHSA-N
Canonical SMILES
C=CCOC(=O)CCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-D-glutamic acid γ-allyl ester is a derivative used in peptide synthesis and bioconjugation applications. Here are some key applications of Fmoc-D-glutamic acid γ-allyl ester:

Peptide Synthesis: Fmoc-D-glutamic acid γ-allyl ester is commonly used as a building block in the synthesis of peptides. Its Fmoc (9-fluorenylmethoxycarbonyl) group allows for easy removal under mildly basic conditions, facilitating the sequential addition of amino acids. This compound enables the introduction of D-glutamic acid with minimal racemization, ensuring the integrity of the synthesized peptide.

Bioconjugation: This compound is utilized in bioconjugation to attach molecules like drugs or fluorescent labels to peptides or proteins. The γ-allyl ester group provides a handle for selective chemical modifications without disrupting the peptide backbone. Such modifications are essential for creating bioconjugates with specific functional properties for applications in therapeutic delivery and bioimaging.

Structure-Function Studies: Researchers use Fmoc-D-glutamic acid γ-allyl ester in structure-function studies to investigate protein-protein interactions. By incorporating this derivative into synthetic peptides, scientists can mimic specific interactions involving D-glutamic acid residues. These studies are crucial for understanding the role of individual amino acids in biological processes and drug design.

Drug Development: The unique properties of Fmoc-D-glutamic acid γ-allyl ester make it valuable in developing peptide-based therapeutics. Its incorporation into peptide chains can enhance drug stability and bioavailability, potentially improving therapeutic outcomes. Drug developers leverage this derivative to design novel peptide drugs with targeted action and reduced side effects.

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