Fmoc-β-cyclopropyl-D-alanine
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Fmoc-β-cyclopropyl-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-005545
CAS number
170642-29-2
Molecular Formula
C21H21NO4
Molecular Weight
351.30
Fmoc-β-cyclopropyl-D-alanine
IUPAC Name
(2R)-3-cyclopropyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-β-cyclopropyl-D-Ala-OH; Fmoc-D-Ala(β-cyclopropyl)-OH
Appearance
White to pale white solid
Purity
≥ 99% (HPLC)
Density
1.291±0.06 g/cm3
Boiling Point
583.5±33.0 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C21H21NO4/c23-20(24)19(11-13-9-10-13)22-21(25)26-12-18-16-7-3-1-5-14(16)15-6-2-4-8-17(15)18/h1-8,13,18-19H,9-12H2,(H,22,25)(H,23,24)/t19-/m1/s1
InChI Key
DRGUEWQZLABTFG-LJQANCHMSA-N
Canonical SMILES
C1CC1CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-β-Cyclopropyl-D-alanine is an important building block in peptide synthesis, particularly in the field of medicinal chemistry. Here are some key applications of Fmoc-β-cyclopropyl-D-alanine:

Peptide Synthesis: Fmoc-β-cyclopropyl-D-alanine is incorporated into peptide sequences to study protein-protein interactions and to develop peptide-based therapeutics. The introduction of this non-natural amino acid can enhance the stability and biological activity of synthetic peptides. Researchers utilize it to create peptides with improved binding affinities and specificities for their targets.

Drug Development: In medicinal chemistry, Fmoc-β-cyclopropyl-D-alanine is used to design and synthesize novel peptide drugs. By incorporating this unique amino acid, scientists can modify the pharmacokinetic properties of peptides, such as their resistance to enzymatic degradation. This can result in the development of peptide therapeutics with longer half-lives and better efficacy.

Structural Biology: Fmoc-β-cyclopropyl-D-alanine is valuable for structural studies of proteins and peptides. By stabilizing certain conformations, it aids in the crystallization and NMR analysis of peptide-protein complexes. This helps researchers elucidate the three-dimensional structures and gain insights into protein folding and function.

Bioconjugation: Fmoc-β-cyclopropyl-D-alanine is used in bioconjugation strategies to attach peptides to various biomolecules such as drugs, imaging agents, or nanoparticles. The cyclopropyl group can provide a site for specific chemical modifications, allowing for the creation of highly targeted delivery systems. This application is essential in developing advanced diagnostics and targeted therapies.

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