(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(naphthalen-2-yl)propanoic acid, CAS No. 138774-94-4

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138774-94-4

Catalog No. EBD13970

CAS 138774-94-4

Name (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(naphthalen-2-yl)propanoic acid

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Basic Information

Synonyms: (R)-N-FMOC-2-Naphthylalanine Fmoc-D-3-(2-Naphthyl)-alanine Fmoc-3-(2-Naphthyl)-D-alanine Fmoc-D-2-Nal-OH Fmoc-2-D-Nal-OH Fmoc-D-2Nal-OH rarechembkpt0102 (r)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-naphthalen-2-yl-propionicacid n-(9-fluorenylmethoxycarbonyl)-2-naphthyl-d-alanine n-alpha-(9-fluorenylmethoxycarbonyl)-3-(2-naphthyl)-d-alanine n-alpha-(9-fluorenylmethyloxycarbonyl)-3-(2-naphthyl)-d-alanine n-alpha-fmoc-beta-(2-naphthyl)-d-alanine n-alpha-(9-fluorenyloxycarbonyl)-d-3-(2-naphthyl)alanine (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(naphthalen-2-yl)propanoicacid

Molecular Formula: C28H23NO4

Molecular Weight: 437.49

MDL Number: MFCD00077044

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

Product Description:

Fmoc-D-β-naphthylalanine is a non-natural, chiral amino acid derivative. Its structure features a β-naphthyl group attached to the side chain of a D-configured alanine core, which is protected at the N-terminus by a 9-fluorenylmethoxycarbonyl (Fmoc) group. This protection is standard in modern solid-phase peptide synthesis (SPPS). This compound serves as a crucial building block in peptide chemistry. The bulky, hydrophobic β-naphthyl side chain is incorporated into synthetic peptides to modulate their physicochemical properties, such as enhancing lipophilicity, influencing secondary structure (e.g., promoting β-sheet formation), and improving binding affinity to hydrophobic pockets on target proteins. It is extensively used in the research and development of therapeutic peptides, peptide hormones, and biochemical probes where specific steric and hydrophobic interactions are desired. The D-configuration of this amino acid makes it valuable for creating peptides resistant to enzymatic degradation, which is a key strategy in developing stable peptide-based pharmaceuticals and diagnostic agents. It is a high-purity reagent specifically designed for Fmoc-based SPPS methodologies.

Physical Properties

Melting Point: 191 °C

Boiling Point: 690.7 °C at 760 mmHg

Flash Point: 371.6 °C

Density: 1.296 g/cm3

Storage: 2-8°C

Analytical Data

Appearance: off-white to light beige crystalline powder