Fmoc-N-Me-D-Phe-OH, CAS No. 138775-05-0

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138775-05-0

Catalog No. EBD2198200

CAS 138775-05-0

Name Fmoc-N-Me-D-Phe-OH

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Basic Information

Synonyms: fmoc-n-methyl-d-phenylalanine fmoc-n-alpha-methyl-d-phenylalanine fmoc-d-mephe-oh n-alpha-(9-fluorenylmethyloxycarbonyl)-n-alpha-methyl-d-phenylalanine n-alpha-(9-fluorenylmethoxycarbonyl)-n-alpha-methyl-phenylalanine n-alpha-(9-fluorenylmethoxycarbonyl)-n-alpha-methyl-d-phenylalanine n-alpha-fmoc-n-alpha-methyl-d-phenylalanine Fmoc-N-Me-D-Phe-Oh (2R)-2-(9H-fluoren-9-ylmethoxycarbonyl-methyl-amino)-3-phenyl-propanoicacid Fmoc-D-N-Me-Phe-OH

Molecular Formula: C25H23NO4

Molecular Weight: 401.45

MDL Number: MFCD00153392

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks

Product Description:

N-Fmoc-N-methyl-D-phenylalanine is a protected, non-proteinogenic amino acid derivative. Its structure features a D-configuration phenylalanine core with an N-methyl substitution and an N-terminal Fmoc (9-fluorenylmethoxycarbonyl) protecting group. This specific combination of stereochemistry (D-form) and N-methylation makes it a valuable chiral building block. This compound is primarily used in solid-phase peptide synthesis (SPPS) as a specialized amino acid residue. The N-methylation enhances the metabolic stability and membrane permeability of the resulting peptides, often reducing their susceptibility to enzymatic degradation. The D-configuration is crucial for designing peptides with specific three-dimensional structures, altered biological activity, or improved pharmacokinetic profiles, which are common goals in the development of therapeutic peptides and peptidomimetics. As a high-purity, protected amino acid, it serves as a critical intermediate for research and development in medicinal chemistry, particularly for creating novel peptide-based drugs, probes, and tools in life sciences. Its use is specialized within peptide synthesis workflows rather than as a general-purpose organic synthesis reagent.

Physical Properties

Boiling Point: 595.439 °C at 760 mmHg

Flash Point: 313.911 °C

Density: 1.261 g/cm3

Storage: 2-8°C