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Bulk Order Fmoc-D-2-Amino-4-Bromo-4-Pentenoic Acid丨CAS 220497-92-7
Fmoc-D-2-Amino-4-Bromo-4-Pentenoic Acid is a specialized non-natural amino acid derivative featuring a D-configured amino acid center, an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protecting group, and a brominated alkene in its side chain. The Fmoc group supports controlled amino protection in peptide synthesis, while the combination of bromine and carbon–carbon double-bond functionality offers opportunities for further chemical transformations. These structural features 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-/m1/s1 |
| InChI Key | BYQROHMHEGJMPD-GOSISDBHSA-N |
| Smiles | C=C(C[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)Br |
| EC No. | |
| MDL No. | MFCD01311777 |
| PubChem CID | 7006565 |
Applications
Applications in Peptide Synthesis
Fmoc-D-2-Amino-4-Bromo-4-Pentenoic Acid can serve as a specialized building block in peptide synthesis, particularly when a non-natural amino acid with defined D-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 enable subsequent coupling steps. Incorporating this residue may introduce distinctive side-chain functionality for investigating peptide structure and properties.
Applications in Medicinal Chemistry
In medicinal chemistry research, this compound can support the preparation of structurally diverse peptide-based molecules and amino-acid-derived compounds. Its D-configuration provides stereochemical variation, while the brominated unsaturated side chain offers potential opportunities for further molecular modification. These features may be useful in the development of analogues and the investigation of structure–activity relationships, depending on the target molecule and synthetic strategy.
Applications in Organic Synthesis and Functionalization
Applications in Chemical Biology Research
Non-natural amino acids with distinctive side-chain functionality can be useful in chemical biology research involving modified peptides and molecular interactions. Fmoc-D-2-Amino-4-Bromo-4-Pentenoic Acid may support the design of peptide structures with altered stereochemistry and reactive side-chain features. Its suitability for a particular biological or labeling workflow should be established through assessment of chemical compatibility and experimental requirements.
