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China Supplier Fmoc-L-2-Amino-4-Bromo-4-Pentenoic Acid丨CAS 220497-60-9
Fmoc-L-2-Amino-4-Bromo-4-Pentenoic Acid is a non-natural amino acid derivative featuring an L-configured amino acid center, an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protecting group, and a brominated unsaturated side chain. The Fmoc group enables temporary amino protection during peptide synthesis, while the carbon–bromine bond and carbon–carbon double bond provide potential sites for further chemical modification. These structural characteristics make this compound relevant to peptide chemistry, medicinal chemistry, and advanced organic synthesis.
Chemical Identifiers
| InChI | InChI=1S/C20H18BrNO4/c1-12(21)10-18(19(23)24)22-20(25)26-11-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17-18H,1,10-11H2,(H,22,25)(H,23,24)/t18-/m0/s1 |
| InChI Key | BYQROHMHEGJMPD-SFHVURJKSA-N |
| Smiles | C=C(C[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)Br |
| EC No. | |
| MDL No. | MFCD01311750 |
| PubChem CID | 2734458 |
Applications
Applications in Peptide Synthesis
Fmoc-L-2-Amino-4-Bromo-4-Pentenoic Acid can serve as a specialized building block for peptide synthesis, particularly when a non-canonical amino acid with L-configuration is required. The Fmoc protecting group is widely used in solid-phase peptide synthesis and can generally be removed under suitable basic conditions to facilitate subsequent coupling steps. Incorporating this residue may introduce distinctive side-chain features into peptide sequences for structural and functional research.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound can support the synthesis of structurally diverse peptide-based molecules and amino-acid-derived compounds. Its defined L-stereochemistry provides a basis for stereochemically specified synthesis, while the brominated unsaturated side chain offers opportunities for additional molecular modification. These features may support analogue preparation and structure–activity relationship studies, depending on the target structure and research objectives.
Applications in Organic Synthesis and Functionalization
Applications in Chemical Biology Research
Non-natural amino acids with distinctive side-chain structures can support chemical biology research involving modified peptides and molecular interactions. Fmoc-L-2-Amino-4-Bromo-4-Pentenoic Acid may be considered for designing peptide structures with specialized chemical functionality. Its suitability for a particular application depends on the intended molecular design, synthesis conditions, and compatibility with the relevant experimental workflow.
