Structure determination of an endogenous sleep-inducing lipid, cis-9-octadecenamide (oleamide): A synthetic approach to the chemical analysis of trace quantities of a natural product

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 580-590

  Cravatt, Benjamin F ^a   Lerner, Richard A ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; OLEAMIDE; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CAT; CEREBROSPINAL FLUID; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030041883     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9532345     Document Type: Article

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35. 2O, 3:1, 10 min, 25 °C, 90%) provided 2(S)-amino-1-hydroxy-3(Z),6(E)-octadecadiene.
36. 4NF (2 equiv, THF, 25 °C, 2 h, 90%); pTsCl (1.1 equiv, pyridine, 0 °C, 12 h, 87%); NaI (2 equiv, acetone, reflux, 2 h, 80%); Ph3P (1.5 equiv, toluene, reflux, 12 h, 86%).
37. 3P (1.5 equiv, toluene, reflux, 12 h, 83%).
38. 3P (1.5 equiv, toluene, reflux, 12 h, 88%).
39. 3P (1.5 equiv, toluene, reflux, 12 h, 86%).
40. 3P (1.5 equiv, toluene, reflux, 12 h, 88%).
41. 3P (1.5 equiv, toluene, reflux, 12 h, 90%).
42. 3P (1.5 equiv, toluene, reflux, 12 h, 89%).
43. In subsequent efforts, the full range of fatty acid amides have been prepared and subjected to comparison analysis: Patterson, J. E. Unpublished studies. Potent inhibitors of oleamide hydrolase: Parterson, J. E.; Ollmann, I. R.; Cravatt, B. F.; Lerner, R. A.; Wong, C.-H.; Boger, D. L. Submitted for publication.
44. In subsequent efforts, the full range of fatty acid amides have been prepared and subjected to comparison analysis: Patterson, J. E. Unpublished studies. Potent inhibitors of oleamide hydrolase: Parterson, J. E.; Ollmann, I. R.; Cravatt, B. F.; Lerner, R. A.; Wong, C.-H.; Boger, D. L. Submitted for publication.
45. We thank Dr. O. Prospero-Garcia, Dr. S. J. Henriksen, and Dr. L. Bibbs for these efforts.
46. 2. The electron energy in EI measurements was 70 eV with 1 scan/s. Retention times: synthetic cis-9-octadecenamide, 16.95 min; natural compound, 16.95 min.
47. The natural compound and synthetic cis-13-docosenamide also exhibited identical elution propeties on TLC.
48. 2CH=CH), 1.69-1.20 (m, 29H).
49. Detailed experimentals for 27-30, 35-38, 41-48, 50-63, 64-66, 68-71, 73-74, 76, 78-81, and 88-92 may be found in the supporting inormation.
50. Roe, E. T.; Scanlan, J. T.; Swern, D. J. Am. Chem. Soc. 1949, 71, 2215.
51. Ramiandrasoa, R.; Descoins, C. Synth. Commun. 1989, 19, 2703.