N-α-(9-Fluorenylmethoxycarbonyl)-β-chloro-D-alanine
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N-α-(9-Fluorenylmethoxycarbonyl)-β-chloro-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-001818
CAS number
1403834-71-8
Molecular Formula
C18H16ClNO4
Molecular Weight
345.77
IUPAC Name
(2S)-3-chloro-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
N-alpha-(9-Fluorenylmethoxycarbonyl)-beta-chloro-D-alanine; Fmoc-D-Ala(3-Cl)-OH; Fmoc-D-Ala(β-Cl)-OH; N-α-(9-Fluorenylmethoxycarbonyl)-3-chloro-D-alanine
Purity
99%
InChI
InChI=1S/C18H16ClNO4/c19-9-16(17(21)22)20-18(23)24-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16H,9-10H2,(H,20,23)(H,21,22)/t16-/m1/s1
InChI Key
NICWPULFDZCIBU-MRXNPFEDSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCl)C(=O)O

N-α-(9-Fluorenylmethoxycarbonyl)-β-chloro-D-alanine, commonly known as Fmoc-β-chloro-D-alanine, is a derivative used in peptide synthesis and biochemical research. Here are some key applications of N-α-(9-Fluorenylmethoxycarbonyl)-β-chloro-D-alanine:

Peptide Synthesis: Fmoc-β-chloro-D-alanine is employed as a building block in the solid-phase synthesis of peptides. Its β-chlorine atom can be used for site-specific modifications or coupling reactions. This allows for the creation of custom peptides with particular functional groups for research and therapeutic purposes.

Protein Engineering: In protein engineering studies, Fmoc-β-chloro-D-alanine can be incorporated into proteins to introduce unique chemical functionalities. These functionalities can be used to study protein interactions, stability, and activity. This application is essential for developing novel proteins with enhanced or altered properties for industrial and medical use.

Pharmaceutical Research: Fmoc-β-chloro-D-alanine is used in the design and synthesis of bioactive peptides which may serve as lead compounds in drug discovery. By modifying peptides with this derivative, researchers can enhance the stability, selectivity, and potency of potential therapeutic agents. This contributes to the development of new drugs for a variety of diseases.

Crystallography Studies: In structural biology, Fmoc-β-chloro-D-alanine can be utilized to create peptides that facilitate protein crystallization. The unique properties of this derivative can improve the crystallization process and the quality of the crystals. This is vital for obtaining high-resolution structures of proteins and understanding their functions and mechanisms.

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