Fmoc-β-(2-furyl)-D-alanine
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Fmoc-β-(2-furyl)-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007497
CAS number
220497-85-8
Molecular Formula
C22H19NO5
Molecular Weight
377.39
Fmoc-β-(2-furyl)-D-alanine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(furan-2-yl)propanoic acid
Synonyms
Fmoc-3-D-Ala(2-furyl)-OH; (R)-2-(Fmoc-amino)-3-(2-furyl)propionic acid
Related CAS
159611-02-6 (L-isomer)
Appearance
White powder
Purity
≥ 98% (HPLC, Chiral purity)
Density
1.318 g/cm3
Melting Point
121.6 °C
Boiling Point
603.3°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C22H19NO5/c24-21(25)20(12-14-6-5-11-27-14)23-22(26)28-13-19-17-9-3-1-7-15(17)16-8-2-4-10-18(16)19/h1-11,19-20H,12-13H2,(H,23,26)(H,24,25)/t20-/m1/s1
InChI Key
AJXDCHXGNUFBRC-HXUWFJFHSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=CO4)C(=O)O

Fmoc-β-(2-furyl)-D-alanine is a derivative used in the synthesis of peptides with broad applications in biochemical research and pharmaceuticals. Here are some key applications of Fmoc-β-(2-furyl)-D-alanine:

Peptide Synthesis: Fmoc-β-(2-furyl)-D-alanine is a valuable building block in solid-phase peptide synthesis. It allows the incorporation of the 2-furyl group into peptide chains, which can impart unique properties to the resulting peptides. This enables the design and synthesis of novel peptides with specific biological activities.

Drug Development: In pharmaceutical research, Fmoc-β-(2-furyl)-D-alanine is used to create peptide-based drugs. The unique structural features of peptides containing this compound can lead to the development of new therapeutics with improved efficacy and stability. This helps in the creation of innovative treatments for various diseases, including cancer and infectious diseases.

Structure-Activity Relationship Studies: Researchers use Fmoc-β-(2-furyl)-D-alanine to investigate the structure-activity relationships (SAR) of peptides. By incorporating this amino acid into different peptide sequences, scientists can study how structural changes affect biological activity. This is crucial for optimizing peptides for therapeutic and biotechnological applications.

Bioconjugation Studies: Fmoc-β-(2-furyl)-D-alanine can be used in bioconjugation experiments to link peptides with other molecules such as drugs, fluorescent probes, or polymers. The 2-furyl group provides a reactive site for chemical modifications, enabling the creation of multifunctional peptide conjugates. These conjugates are useful in drug delivery systems, imaging, and diagnostic applications.

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