Fmoc-N-Me-Val-OH Chemical Properties

Melting point:

187-190 °C

alpha 

-68 º (c=1% in DMF)

Boiling point:

527.6±29.0 °C(Predicted)

Density 

1.214±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

3.92±0.10(Predicted)

form 

Powder

color 

White

optical activity

[α]20/D 68.0±3°, c = 1% in DMF

Water Solubility 

Slightly soluble in water and dimethyl formamide.

BRN 

4560212

InChI

InChI=1S/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

InChIKey

YCXXXPZNQXXRIG-IBGZPJMESA-N

SMILES

C(O)(=O)[C@H](C(C)C)N(C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)C

CAS DataBase Reference

84000-11-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2924297099

MSDS

• Language:English Provider:SigmaAldrich

Fmoc-N-Me-Val-OH Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

N-Fmoc-N-methyl-L-valine (Fmoc-N-Me-Val-OH) is used as enzyme substrates and reagents, culture media additives, dyes, stains and indicators. It is also involved in the preparation of N-methylated peptides.

General Description

Fmoc-N-Me-Val-OH is a modified peptide. It is provided as a white powder with a molecular formula of C21H23NO4 and a molecular weight of 353.41. This compound is indispensable in peptide and peptidomimetic synthesis applications within the pharmaceutical, biotechnology and chemical sectors.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl(methyl)amino)-3-methylbutanoic acid from (S)-3-Fmoc-4-isopropyl-5-oxoxoxazolidine was as follows: the Fmoc-valyl oxazolidinone (2.80 g, 8.00 mmol) was dissolved in chloroform (40 mL). To this solution, trifluoroacetic acid (1.85 mL, 24.0 eq.) and triethylsilane (3.83 mL, 24.0 eq.) were added sequentially. The reaction mixture was stirred at room temperature until the reaction was complete (24-72 hours). Upon completion of the reaction, the solution was concentrated and partitioned between ether and 5% sodium bicarbonate solution. The aqueous phases were combined and the pH was adjusted to 2 with 5 M hydrochloric acid, followed by extraction with ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, and concentrated to give Fmoc-N-methylvaline (4) as a white solid (2.35 g, 83% yield).Fmoc-N-methylvaline was recrystallized by ethyl acetate to give white acicular crystals: melting point 186-187 °C (literature value 33: 185-187 °C); low resolution mass spectra (ESI) m/z [M + H ]+ 354.1 (100%), [M + Na]+ 376.1 (61%); IR spectrum (NaCl) νmax (cm-1) 3420 (broad, OH), 2964 (aliphatic CH), 1700 (C=O), 1445, 1305 (C=C); 1H NMR (300 MHz, CDCl3) δH (ppm) 7.63 (2H, d, J=7.5 Hz, ArH), 7.46 (2H, d, J=6.9 Hz, ArH), 7.26 (2H, t, J=7.2 Hz, ArH), 7.17 (2H, t, J=7.5 Hz, ArH), 4.28 (2H, m, CHCH2O), 4.22 (1H, m, (Ar)2CHCH2). 4.13 (1H, m, NCHCO), 2.79 (3H, d, J=4.2 Hz, NCH3), 2.02 (1H, m, CH3CHCH3), 0.88 (3H, dd, J=6.6, 19.2 Hz, CH3CHCH3), 0.72 (3H, dd, J=6.6, 13.8 Hz, CH3CHCH3) ( IR and 1H NMR data are consistent with literature reports); 13C NMR (75 MHz, CDCl3) δC (ppm) 175.5, 159.6, 146.6, 143.9, 130.4, 129.7, 127.7, 122.6, 70.3, 66.9, 49.9, 33.1, 30.2, 22.5, 21.7.

References

[1] Journal of Organic Chemistry, 2005, vol. 70, # 17, p. 6918 - 6920
[2] European Journal of Organic Chemistry, 2013, # 21, p. 4509 - 4513
[3] Tetrahedron, 2014, vol. 70, # 14, p. 2351 - 2358

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