84000-11-3

Basic information

• Product Name: Fmoc-N-methyl-L-valine
• Synonyms: FMOC-MEVAL-OH;FMOC-N-ALPHA-METHYL-L-VALINE;FMOC-N-ME-VALINE;FMOC-N-ME-VAL-OH;FMOC-N-METHYL-L-VALINE;FMOC-N-ME-L-VAL-OH;FMOC-L-MEVAL-OH;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-ALPHA-METHYL-L-VALINE
• CAS NO: 84000-11-3
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.41
• Product Categories: Amino Acids;Valine [Val, V];N-Methyl Amino Acids;Fmoc-Amino acid series
• Mol File: 84000-11-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 187-190 °C
• Boiling Point: 527.6 °C at 760 mmHg
• Flash Point: 272.9 °C
• Appearance: White/Powder
• 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)
• Water Solubility: Slightly soluble in water and dimethyl formamide.
• BRN: 4560212
• CAS DataBase Reference: Fmoc-N-methyl-L-valine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-N-methyl-L-valine(84000-11-3)
• EPA Substance Registry System: Fmoc-N-methyl-L-valine(84000-11-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 84000-11-3(Hazardous Substances Data)

Usage

Description

Fmoc-N-methyl-L-valine, also known as N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-valine, is a synthetic amino acid derivative that plays a crucial role in various applications across different industries. It is characterized by the presence of a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group and a methyl group on the nitrogen atom, which imparts unique properties to this compound.

Uses

Used in Pharmaceutical Industry:
Fmoc-N-methyl-L-valine is used as a building block for the synthesis of N-methylated peptides, which are important in the development of novel therapeutic agents. These peptides have potential applications in the treatment of various diseases, including cancer and neurological disorders, due to their unique structural and functional properties.
Used in Biochemical Research:
Fmoc-N-methyl-L-valine serves as an enzyme substrate and reagent in biochemical research, enabling the study of enzyme specificity, kinetics, and mechanisms. Its unique structure allows for the investigation of the role of N-methylation in protein function and regulation.
Used in Cell Culture:
As a culture media additive, Fmoc-N-methyl-L-valine supports the growth and maintenance of various cell types, particularly those requiring specific amino acid supplementation for optimal growth and function.
Used in Analytical Chemistry:
Fmoc-N-methyl-L-valine is utilized as a dye, stain, or indicator in analytical chemistry, where its unique spectral properties can be employed for the detection, quantification, or visualization of specific compounds or processes.
Overall, Fmoc-N-methyl-L-valine is a versatile compound with applications in various fields, including pharmaceuticals, biochemical research, cell culture, and analytical chemistry, due to its unique structural features and functional properties.

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-/m0/s1

Upstream product

• 67-56-1 methanol 
• 72-18-4 L-valine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 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 
• 186581-53-3 diazomethane 
• 270073-00-2 3-methyl-2-(4-nitrophenylsulphonamido)butanoic acid 
• 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 
• 1360075-55-3 H-Asp(OtBu)-D-Tyr(tBu)-MeVal-Arg(Pbf)-Gly-OH 
• 1360075-54-2 cyclo(Asp(OtBu)-D-Tyr(tBu)-MeVal-Arg(Pbf)-Gly) 
• 1426327-09-4 C₇₅H₁₂₂N₂O₇ 
• 1579990-03-6 C₅₉H₉₂N₈O₁₁ 

Relevant articles and documents

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

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