Fmoc-D-aspartic acid β-allyl ester
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Fmoc-D-aspartic acid β-allyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-003633
CAS number
177609-12-0
Molecular Formula
C22H21NO6
Molecular Weight
395.40
Fmoc-D-aspartic acid β-allyl ester
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-prop-2-enoxybutanoic acid
Synonyms
Fmoc-D-Asp(OAll)-OH; (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(allyloxy)-4-oxobutanoic acid
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.286±0.06 g/cm3(Predicted)
Boiling Point
638.5±55.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C22H21NO6/c1-2-11-28-20(24)12-19(21(25)26)23-22(27)29-13-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h2-10,18-19H,1,11-13H2,(H,23,27)(H,25,26)/t19-/m1/s1
InChI Key
FBNFRRNBFASDKS-LJQANCHMSA-N
Canonical SMILES
C=CCOC(=O)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-D-aspartic acid β-allyl ester plays a pivotal role in peptide synthesis and medicinal chemistry, offering a plethora of applications. Here are four key applications presented with high perplexity and burstiness:

Peptide Synthesis: A cornerstone in solid-phase peptide synthesis (SPPS), Fmoc-D-aspartic acid β-allyl ester facilitates the incorporation of D-aspartic acid residues into peptide chains. The Fmoc protecting group allows for selective deprotection during synthesis cycles, enabling the meticulous construction of intricate peptides with unparalleled precision and purity.

Drug Development: Within the realm of medicinal chemistry, Fmoc-D-aspartic acid β-allyl ester emerges as a fundamental building block for crafting peptidomimetic drugs and inhibitors. By integrating this compound, researchers can engineer molecules that mimic natural peptides while boasting augmented stability and bioactivity. This innovation is pivotal in the development of novel therapeutic agents aimed at combatting a myriad of diseases.

Structural Biology: Delving into the domain of structural biology, Fmoc-D-aspartic acid β-allyl ester serves as a crucial tool for exploring the structural nuances of proteins and peptides. Harnessing the power of D-aspartic acid in peptides sheds light on the influence of stereochemistry on protein folding and stability. This knowledge is instrumental in unraveling protein functionality and architecting superior therapeutic proteins.

Bioconjugation: Beyond its conventional applications, this compound finds utility in bioconjugation techniques for fusing peptides with diverse molecules like fluorescent dyes or drugs. The β-allyl ester furnishes a functional handle for subsequent modifications and conjugation reactions, propelling the development of sophisticated biomolecular probes and targeted drug delivery systems.

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