138775-05-0

Basic information

• Product Name: Fmoc-N-methyl-D-phenylalanine
• Synonyms: FMOC-N-METHYL-D-PHENYLALANINE;FMOC-N-ME-D-PHE-OH;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
• CAS NO: 138775-05-0
• Molecular Formula: C₂₅H₂₃NO₄
• Molecular Weight: 401.45
• EINECS: 1533716-785-6
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 138775-05-0.mol

Chemical Properties

• Boiling Point: 595.439 °C at 760 mmHg
• Flash Point: 313.911 °C
• Appearance: /Solid
• Density: 1.261 g/cm³
• Vapor Pressure: 5.02E-15mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: 2-8°C
• PKA: 3.78±0.10(Predicted)
• BRN: 8441627
• CAS DataBase Reference: Fmoc-N-methyl-D-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-N-methyl-D-phenylalanine(138775-05-0)
• EPA Substance Registry System: Fmoc-N-methyl-D-phenylalanine(138775-05-0)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 138775-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-N-methyl-D-phenylalanine is used as an intermediate for the synthesis of fluorinated analogs of pepstatin A and grassystatin A. These analogs function as inhibitors of aspartic protease enzymes, which are crucial in various biological processes and are often targeted for therapeutic intervention in diseases such as cancer, autoimmune disorders, and viral infections.
The application of Fmoc-N-methyl-D-phenylalanine in the pharmaceutical industry is primarily due to its ability to facilitate the development of novel inhibitors that can potentially treat a wide range of diseases by targeting specific enzymes involved in their pathogenesis.
Additionally, Fmoc-N-methyl-D-phenylalanine can be utilized in the design and synthesis of other bioactive peptides and peptidomimetics, which may have potential applications in drug discovery and development, as well as in the study of protein-protein interactions and enzyme mechanisms.

InChI:InChI=1/C25H23NO4/c1-26(23(24(27)28)15-17-9-3-2-4-10-17)25(29)30-16-22-20-13-7-5-11-18(20)19-12-6-8-14-21(19)22/h2-14,22-23H,15-16H2,1H3,(H,27,28)/t23-/m1/s1

Upstream product

• 84000-03-3 9H-fluoren-9-ylmethyl (S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylate 
• 35661-40-6 N-Fmoc L-Phe 
• 852852-85-8 N-nosyl-D-phenylalanine 
• 186581-53-3 diazomethane 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 56564-52-4 N-methyl-D-phenylalanine 
• 18942-49-9 Boc-D-Phe-OH 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 37553-65-4 N-tert-butoxycarbonyl-N-methyl-D-phenylalanine 

Downstream Products

• 1321842-01-6 NH₂-Lys(Cbz)-Lys(Boc)-Val-N-Me-D-Phe-Phe-OH 
• 1321841-83-1 NH₂-Val-NMe-D-Phe-(Boc)Lys-(Cbz)Lys-Leu-OH 
• 1321841-92-2 NH₂-(Boc)Lys-NMe-D-Phe-Phe-(Cbz)Lys-Leu-OH 
• 1321841-84-2 macrocyle Val-NMe-D-Phe-(Boc)Lys-(Cbz)Lys-Leu 
• 1321841-86-4 macrocycle Val-NMe-D-Phe-Lys-(Cbz)Lys-Leu 
• 1374429-75-0 NH-Me-D-Phe-D-Lys(2-Cl-Z)-Val-Lys(Boc)-Phe-OH 
• 1374429-82-9 NH₂-Phe-Me-D-Phe-D-Lys(2-Cl-Z)-Lys(Boc)-Leu-OH 
• 1321842-03-8 macrocycle (Cbz)Lys-(Boc)Lys-Val-NMe-D-Phe-Phe 

Relevant articles and documents

First total synthesis of hoshinoamide A

Hoshinoamides A, B and C, linear lipopeptides, were isolated from the marine cyanobacterium Caldora penicillata, with potent antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum. Herein, we describe the first total synthesis of hosh

Isostearyl Mixed Anhydrides for the Preparation of N-Methylated Peptides Using C-Terminally Unprotected N-Methylamino Acids

Sustainable and efficient manufacturing methods for N-methylated peptides remain underexplored despite growing interest in therapeutic N-methylated peptides within the pharmaceutical industry. A methodology for the coupling of C-terminally unprotected N-methylamino acids mediated by an isostearic acid halide (ISTAX) and silylating reagent has been developed. This approach allows for the coupling of a wide variety of amino acids and peptides in high yields under mild conditions without the need for a C-terminal deprotection step in the process of C-terminal elongation. These advantages make this a useful synthetic method for the production of peptide therapeutics and diagnostics containing N-methylamino acids.

Iridium-Catalyzed Asymmetric Hydrogenation of N-Alkyl α-Aryl Furan-Containing Imines: an Efficient Route to Unnatural N-Alkyl Arylalanines and Related Derivatives

High throughput experimentation (HTE) has enabled the rapid identification of ligand/precatalyst combinations that facilitate highly enantioselective hydrogenations of prochiral N-alkyl α-aryl ketimines containing a furyl moiety. The chiral amines obtained have proven to be modular precursors in the synthesis of unnatural mono N-alkylated arylalanines and related derivatives. (Figure presented.).

Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-α-amino acids

(Chemical Equation Presented) We report here a convenient and simple solid-phase synthesis of N-nosyl-N-methyl-α-amino acids and N-Fmoc-N-methyl-α-amino acids, important building blocks for the synthesis of conformationally restricted and protease-resista

Synthesis of 9-Fluorenylmethyloxycarbonyl-Protected N-Alkyl Amino Acids by Reduction of Oxazolidinones

A new two-step synthesis of Fmoc-protected N-alkyl amino acids has been developed.The first step involves acid-catalyzed condensation of an Fmoc-protected amino acid with an aldehyde to form an oxazolidinone.This intermediate is then reduced with triethyl