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

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

Uses

Used in Pharmaceutical Industry:
Fmoc-N-methyl-D-valine is used as a building block for the synthesis of custom peptides for drug development. Its unique structure and properties allow for the creation of complex peptide sequences that can be used as therapeutic agents or for research purposes.
Used in Research Applications:
Fmoc-N-methyl-D-valine is used as a component in the synthesis of custom peptides for various research applications. Its versatility in peptide synthesis enables the development of novel peptide sequences for studying biological processes and mechanisms.
Used in Biochemical Applications:
Fmoc-N-methyl-D-valine is used as a key component in the synthesis of peptides for biochemical applications. Its unique properties allow for the creation of peptides with specific functions, such as enzyme inhibitors, receptor agonists or antagonists, and other bioactive molecules.

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

• 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 
• 68858-20-8 Fmoc-Val-OH 
• 1220527-59-2 N-Fmoc-N-methyl-L-valine benzhydryl ester 
• 1208119-51-0 N-methyl-N-nosyl-L-valine phenacyl ester 
• 84000-01-1 9H-fluoren-9-ylmethyl (S)-4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylate 

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 
• 1426327-09-4 C₇₅H₁₂₂N₂O₇ 
• 1579990-03-6 C₅₉H₉₂N₈O₁₁ 
• 1380421-53-3 C₄₃H₆₅N₉O₁₁S 
• 1360075-54-2 cyclo(Asp(OtBu)-D-Tyr(tBu)-MeVal-Arg(Pbf)-Gly) 
• 1360075-55-3 H-Asp(OtBu)-D-Tyr(tBu)-MeVal-Arg(Pbf)-Gly-OH 

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

A total synthesis of a highly N-methylated cyclodepsipeptide [2S,3S-Hmp]-aureobasidin L using solid-phase methods

[2S,3S-Hmp]-Aureobasidin L 2 has been successfully synthesised through a combination of solution- and solid-phase peptide synthesis. All of the Fmoc-protected residues including a depsidipeptide, Fmoc-MeVal-Hmp-OH, were prepared in solution phase. Chain e

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

A preparation of N-Fmoc-N-methyl-α-amino acids and N-nosyl-N-methyl-α-amino acids

A convenient route for the synthesis of lipophilic N-Fmoc-N-methyl-α- amino acids and N-nosyl-N-methyl-α-amino acids, interesting building blocks to be used for the preparation of N-methylated peptides, is presented. Both nosyl- and Fmoc-protected monomer

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.

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

Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis

N-Methyl amino acids and their Fmoc derivatives are synthesized in high yield and purity on solid support using the Fukuyama amine synthesis protocol.

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