N-FORMYL-L-LEUCINE Chemical Properties

Melting point:

142 °C

Boiling point:

284.67°C (rough estimate)

Density 

1.2013 (rough estimate)

refractive index 

-39.5 ° (C=1, H2O)

storage temp. 

-20°C

solubility 

Ethanol (Sparingly), Methanol (Slightly)

form 

powder

pka

3.51±0.21(Predicted)

color 

white

Water Solubility 

29.45g/L(temperature not stated)

InChI

InChI=1S/C7H13NO3/c1-5(2)3-6(7(10)11)8-4-9/h4-6H,3H2,1-2H3,(H,8,9)(H,10,11)/t6-/m0/s1

InChIKey

HFBHOAHFRNLZGN-LURJTMIESA-N

SMILES

C(O)(=O)[C@H](CC(C)C)NC=O

CAS DataBase Reference

6113-61-7(CAS DataBase Reference)

Safety Information

WGK Germany 

1

HazardClass 

IRRITANT

HS Code 

2924297099

MSDS

• Language:English Provider:SigmaAldrich

N-FORMYL-L-LEUCINE Usage And Synthesis

Chemical Properties

White Solid

Uses

A synthetic substrate of the lipase inhibitor lipstatin.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure: L-leucine hydrochloride (1 eq.), formic acid (5 eq.), sodium bicarbonate (10 eq.) and glycerol ketone-oxide 1 (2 eq.) were dissolved in H2O (0.2-0.3 M), followed by the addition of EDCI (2 eq.). The reaction mixture was stirred for 3 h. Upon completion of the reaction, it was quenched with 1% HCl aqueous solution. The aqueous phase was extracted with EtOAc (or CHCl3, or CHCl3-MeOH (10/1). The organic extracts were combined and dried with Na2SO4, followed by vacuum evaporation of the solvent. Purification by silica gel chromatography (or Sephadex LH20) afforded N-formyl-DL-leucine (see Table 1 for yields). Similarly, the N-formylation reaction was carried out using oxide 1 in DMF-H2O (9/1).

References

[1] Tetrahedron Letters, 2013, vol. 54, # 16, p. 2077 - 2081

N-FORMYL-L-LEUCINE(6113-61-7)Related Product Information

• [2R-[1(S*),2R*,3S*]]- N-Formyl-L-Leucine 1-[3-Carboxy-2-hydroxynonyl]dodecyl Ester,N-Formyl-L-leucine (1S)-1-[(2S,3S)-3-carboxy-2-hydroxynonyl]dodecyl Ester
• AHLBNYSZXLDEJQ-FICKONGGSA-N
• Orlistat Impurity 32
• (S,S,R,S)-Orlistat
• N-ForMyl-L-leucine [S-(E)]-1-(2-Nonenyl)dodecyl Ester
• Orlistat Tetradecyl Ester
• Isopentyl (2R)-Orlistat Tetradecyl Ester
• [2S-[2α(R*),3β]]-N-ForMyl-
• (2S,3R,5S)-5-[(N-Formyl-L-leucyl)oxy]-2-hexyl-3-hydroxyhexadecanoic Acid (Orlistat Impurity)
• N-ForMyl-
• Orlistat Impurity 23
• (3S,4S)-3-Hexyl-4-[(S)-2-hydroxytridecyl]-2-oxetanone
• AHLBNYSZXLDEJQ-HDVRVJOHSA-N
• Orlistat Impurity 31
• Lipstatin
• (2S,3S,5S)-2-Hexyl-3,5-dihydroxyhexadecanoic Acid
• Orlistat Dimer Impurity
• Diisopropyl azodicarboxylate