Modular approach to the synthesis of unsaturated 1-monoacyl glycerols

Synlett

Volumn , Issue 8, 2004, Pages 1339-1342

  Coleman, Bridgett E ^a   Cwynar, Valerie ^a   Hart, David J ^a   Havas, Fabien ^a   Jakkam, Madan Mohan ^a   Patterson, Suzanne ^a   Ridenour, Sam ^a   Schmidt, Michael ^a   Smith, Eboney ^a   Wells, Angela J ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

1 monoacylglycerol; Diimide reduction; Protein crystallization; Suzuki coupling; Vinyl iodide

Indexed keywords

MONOACYLGLYCEROL; UNSATURATED FATTY ACID;

ARTICLE; CRYSTALLIZATION; ESTERIFICATION; GEOMETRY; REDUCTION; SUZUKI REACTION; SYNTHESIS;

EID: 3142751258     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-825616     Document Type: Article

References (12)

1. Caffrey, M. Structural Biology 2000, 10, 486.
2. Jensen, R. G.; Pitas, R. E. Adv. Lipid. Res. 1977, 14, 213.
3. In this paper we will refer to 1-MAGs in [N.T] space where N = neck length and T = tail length. For example the 1-MAG in which the fatty acid component is oleic acid will be called [9.9].
4. For example, in our hands, alkyne hydrogenation strategies provided cis fatty acids with 2-10% contamination from the corresponding trans fatty acids. In one case we examined differences in oxidation state of the carboxyl terminus at the stage of hydrogenation and catalyst type but were unable to routinely obtain the olefin homogeneities of greater than 99% desired for protein crystallization studies. See: Valicenti, A. M.; Pusch, F. M.; Holman, R. T. Lipids 1985, 20, 234.
5. Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314.
6. Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083.
7. For a review of the Suzuki coupling using alkylboranes see: Trauner, D.; Chemler, S. R.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2001, 40, 4544.
8. For the conditions and additives used in this study see: Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818.
9. 4Na: 379.2819; found: 379.2845.
10. 13C NMR spectroscopy. For example the olefinic carbons in the cis isomer appeared at δ = 130.0 and 130.5 ppm whereas the olefinic carbons in the trans isomer appeared at δ = 131.0 and 131.5 ppm.
11. 13C NMR spectra.
12. 2) and δ = 75 ppm (OCH).