4-[(Dithylphosphono)difluoromethyl]-N-(fluoren-9-ylmethoxycarbonyl)-L-phenylalamine, CAS No. 160751-44-0

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160751-44-0

Catalog No. EBD21302

CAS 160751-44-0

Name 4-[(Dithylphosphono)difluoromethyl]-N-(fluoren-9-ylmethoxycarbonyl)-L-phenylalamine

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Basic Information

Synonyms: 4-(difluorophosphonomethyl)-n-[(9h-fluoren-9-ylmethoxy)carbonyl]-l-phenylalanine (4-(diethylphosphono)difluoromethyl)-n-(fluoren-9-yl-methoxycarbonyl)-l-phenylalanine n-alpha-9-fluorenylcarbonyl-4-(diethylphosphonodifluoromethyl)-l-phenylalanine n-alfa-fmoc-4-(phosphonodifluoromethyl)-l-phenylalanine n-alpha-fmoc-4-(phosphonodifluoromethyl)-l-phenylalanine 4-(diethylphosphono)difluoromethyl)-n-(fluoren-9-yl-methoxycarbony)-l-phenylalanine n-alfa-fluorenylcarbonyl-4-(diethylphosphonodifluoromethyl)-l-phenylalanine 4-[(DITHYLPHOSPHONO)DIFLUOROMETHYL]-N-(FLUOREN-9-YLMETHOXYCARBONYL)-L-PHENYLALAMINE 4-(DIETHYLPHOSPHONO)DIFLUOROMETHYL)-N- Fmoc-Phe(CF2PO3)-OH

Molecular Formula: C29H30F2NO7P

Molecular Weight: 573.52

MDL Number: MFCD01317828

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Targeted Protein Degradation Tools > Linkers

Product Description:

N-α-Fmoc-4-(phosphonodifluoromethyl)-L-phenylalanine is a non-natural, fluorinated amino acid derivative. Its structure features an L-phenylalanine backbone with an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protecting group and a phosphonodifluoromethyl (-CF2PO3H2) substituent at the para-position of the phenyl ring. This unique combination of a protected α-amino acid and a bioisosteric difluorophosphonate group makes it a specialized building block. This compound is primarily used in solid-phase peptide synthesis (SPPS) for the incorporation of a phosphonate mimic into peptide sequences. The difluorophosphonate moiety is a potent and stable bioisostere for phosphate groups, making it valuable in the development of peptide-based enzyme inhibitors, particularly targeting phosphatases and kinases. Furthermore, its structural features, including the aromatic ring and the polar, metabolically stable -CF2PO3H2 group, also make it a candidate for designing specialized linkers in targeted drug delivery systems, such as antibody-drug conjugates (ADCs) or proteolysis-targeting chimeras (PROTACs), where stability and specific interactions are crucial. The Fmoc protection allows for standard SPPS protocols, while the difluorophosphonate group introduces significant polarity and potential for ionic interactions, influencing the peptide's solubility, binding affinity, and metabolic stability. Handling requires standard precautions for amino acid derivatives and phosphonate compounds.

Physical Properties

Boiling Point: 721.413°C at 760 mmHg

Flash Point: 390.097°C

Density: 1.476 g/cm3