Fmoc-β-chloro-L-alanine
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Fmoc-β-chloro-L-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-005543
CAS number
212651-52-0
Molecular Formula
C18H15NO4Cl
Molecular Weight
345.70
Fmoc-β-chloro-L-alanine
IUPAC Name
(2R)-3-chloro-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-β-Chloro-L-Ala-OH; Fmoc-3-Chloro-L-alanine
Appearance
White solid
Purity
≥ 99% (HPLC)
Storage
Store at 2-8°C
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-/m0/s1
InChI Key
NICWPULFDZCIBU-INIZCTEOSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCl)C(=O)O

Fmoc-β-chloro-L-alanine is a versatile reagent used in peptide synthesis and medicinal chemistry. Here are some key applications of Fmoc-β-chloro-L-alanine:

Peptide Synthesis: Fmoc-β-chloro-L-alanine is crucial for the synthesis of modified peptides. It introduces a chloro group that can be further manipulated for site-specific modifications or functionalizations. This versatility allows researchers to create peptides with unique properties for biochemical and pharmacological studies.

Medicinal Chemistry: In drug development, Fmoc-β-chloro-L-alanine serves as a building block for designing molecules with potential therapeutic effects. Its chloro substituent can participate in various chemical reactions, facilitating the development of protease inhibitors or other bioactive compounds. This application is essential for exploring new drug candidates and optimizing their efficacy and safety.

Protein Engineering: Fmoc-β-chloro-L-alanine is used in the design of engineered proteins with novel functionalities. By incorporating this modified amino acid into protein sequences, scientists can study the effects of specific alterations on protein structure and function. This approach is particularly useful in creating proteins with enhanced stability, activity, or binding affinity for biotechnological applications.

Chemical Biology: Researchers leverage Fmoc-β-chloro-L-alanine in chemical biology to probe cellular processes. The chloro group can be converted into reactive intermediates for cross-linking studies, allowing for the identification and mapping of protein-protein interactions. This technique is vital for understanding the molecular mechanisms underlying complex biological systems.

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