103478-58-6

Basic information

• Product Name: Fmoc-N-methyl-D-valine
• Synonyms: N-ALPHA-FMOC-N-ALPHA-METHYL-D-VALINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-ALPHA-METHYL-D-VALINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-ALPHA-METHYL-D-VALINE;Fmoc-D-N-Me-Val-OH;FMOC-N-ME-D-VAL 98.5+%;Fmoc-D-N-Me-Ala-OH;N-(9-Fluorenylmethyloxycarbonyl)-N-methyl-D-valine;(R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)(Methyl)aMino)-3-Methylbutanoic acid
• CAS NO: 103478-58-6
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.41
• Product Categories: Amino Acids;N-Methyl Amino Acids;Amino Acid Derivatives
• Mol File: 103478-58-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 527.6 °C at 760 mmHg
• Flash Point: 272.9 °C
• Appearance: /Solid
• Density: 1.214 g/cm³
• Vapor Pressure: 5.83E-12mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: 2-8°C
• PKA: 3.92±0.10(Predicted)
• CAS DataBase Reference: Fmoc-N-methyl-D-valine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-N-methyl-D-valine(103478-58-6)
• EPA Substance Registry System: Fmoc-N-methyl-D-valine(103478-58-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 103478-58-6(Hazardous Substances Data)

Usage

General Description

Fmoc-N-methyl-D-valine is a chemical compound that belongs to the family of N-protected amino acids and is commonly used in peptide synthesis. It is a derivative of the amino acid valine, with a methyl group added to the nitrogen atom. The Fmoc group serves as a protecting group for the amine functional group, allowing for selective deprotection during peptide synthesis. Fmoc-N-methyl-D-valine is often used in the creation of custom peptides for research, drug development, and other biochemical applications. Its unique structure and properties make it a valuable building block in the development of complex peptide sequences.

InChI:InChI=1/C21H23NO4/c1-13(2)19(20(23)24)22(3)21(25)26-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,13,18-19H,12H2,1-3H3,(H,23,24)/t19-/m1/s1

Upstream product

• 84000-01-1 9H-fluoren-9-ylmethyl (S)-4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylate 
• 68858-20-8 Fmoc-Val-OH 
• 67-56-1 methanol 
• 72-18-4 L-valine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 186581-53-3 diazomethane 
• 270073-00-2 3-methyl-2-(4-nitrophenylsulphonamido)butanoic acid 
• 1208119-51-0 N-methyl-N-nosyl-L-valine phenacyl ester 
• 1220527-59-2 N-Fmoc-N-methyl-L-valine benzhydryl ester 

Downstream Products

• 205498-84-6 [(S)-1-((S)-2-{(S)-2-[(1R,2R)-1-Methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 926016-58-2 H-Tyr-NMeVal-Phe-Leu-NH₂ 
• 1301720-98-8 H-Tyr-MeVal-MeVal-Phe-Leu-NH₂ 

Relevant articles and documents

An improved synthesis of Fmoc-N-methyl-α-amino acids

A highly efficient and environmentally more benign synthesis of Fmoc-N-methyl-α-amino acids from the corresponding Fmoc-amino acid, via intermediate 5-oxazolidinones, has been developed by using Lewis acid catalysis for the reductive opening of the oxazol

Fluorenylmethoxycarbonyl-N-methylamino acids synthesized in a flow tube-in-tube reactor with a liquid-liquid semipermeable membrane

Both steps of the N-methylation of 9-fluorenylmethoxycarbonyl (Fmoc) amino acids were carried out in a microstructured tube-in-tube reactor equipped with a semipermeable Teflon AF 2400 membrane as the inner tubing. In the first step, gaseous formaldehyde

An efficient preparation of N-Methyl-α-amino acids from N-Nosyl-α-amino acid phenacyl esters

Chemical Equation Presented In this paper we describe a simple and efficient solution-phase synthesis of N-methyl-TV-nosyl-α-amino acids and N-Fmoc-N-methyl-α-amino acids. This represents a very important application in peptide synthesis to obtain N-methylated peptides in both solution and solid phase. The developed methodology involves the use of N-nosyl-α-amino acids with the carboxyl function protected as a phenacyl ester and the methylating reagent diazomethane. An important aspect of this synthetic strategy is the possibility to selectively deprotect the carboxyl function or alternatively both amino and carboxyl moieties by using the same reagent with a different molar excess and under mild conditions. Furthermore, the adopted procedure keeps unchanged the acid-sensitive side chain protecting groups used in Fmoc-based synthetic strategies.