Separation of polyunsaturated fatty acids by selective inclusion in guanidinium-1,5-naphthalenedisulfonate-2-methoxyethanol host networks

Biotechnology and Bioengineering

Volumn 92, Issue 5, 2005, Pages 532-540

  Voogt, Jason N ^a   Blanch, Harvey W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Hydrogen bonded networks; Inclusion compounds; Omega 3 fatty acids; Polyunsaturated fatty acids

Indexed keywords

ALCOHOLS; CRYSTALLINE MATERIALS; CRYSTALLIZATION; ESTERS; HYDROGEN BONDS; POROUS MATERIALS;

HYDROGEN-BONDED NETWORKS; INCLUSION COMPOUNDS; OMEGA-3 FATTY ACIDS; POLYUNSATURATED FATTY ACIDS;

FATTY ACIDS;

2 METHOXYETHANOL; ALCOHOL DERIVATIVE; FATTY ACID ESTER; GUANIDINE DERIVATIVE; LINOLEIC ACID; METHANOL; MONOUNSATURATED FATTY ACID; NAPHTHALENE DERIVATIVE; OLEIC ACID; OMEGA 3 FATTY ACID; POLYUNSATURATED FATTY ACID; SOLVENT; STEARIC ACID; SULFONIC ACID DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; POROSITY; SEPARATION TECHNIQUE; SYNTHESIS;

ABSORPTION; CHEMICAL FRACTIONATION; CRYSTALLIZATION; ESTERS; FATTY ACIDS, UNSATURATED; GUANIDINE; HYDROGEN BONDING; NAPHTHALENESULFONATES; POROSITY; SOLUBILITY;

EID: 29544433327     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/bit.20649     Document Type: Article

References (25)

1. Alkio M, Gonzalez C, Jantti M, Aaltonen O. 2000. Purification of polyunsaturated fatty acid esters from tuna oil with supercritical fluid chromatography. J Am Oil Chemists Soc 77(3):315-321.
2. Allcock HR, Allen RW, Bissell EC, Smeltz LA, Teeter M. 1976. Molecular motion and molecular separation in cyclophosphazene clathrates. J Am Chem Soc 98:5120-5125.
3. Allcock HR, Sunderland NJ, Primrose AP, Rheingold AL, Guzei IA, Parvez M. 1999. A new host for polymer and small-molecule clathration. Chem Mater 11(9):2478-2485.
4. Applegate KR, Glomset JA. 1986. Computer-based modeling of the conformation and packing properties of docosahexaenoic acid. J Lipid Res 27:658-680.
5. Caira MR, Home A, Nassimbeni LR, Toda F. 1997. Inclusion and separation of picoline isomers by a diol host compound. J Mater Chem 7(10):2145-2149.
6. Davis ME, Pun SH, Bellocq NC, Reineke TM, Popielarski SR, Mishra S, Heidel JD. 2004. Self-assembling nucleic acid delivery vehicles via linear, water-soluble, cyclodextrin-containing polymers. Curr Med Chem 11(2):179-197.
7. De Swaaf ME, Sijtsma L, Pronk JT. 2003. High-cell-density fed-batch cultivation of the docosahexaenoic acid producing marine alga Crypthecodinium cohnii. Biotechnol Bioeng 81(6):666-672.
8. Evans RW, Tinoco J. 1978. Monolayers of sterols and phosphatidylcholines containing a 20-carbon chain. Chem Phys Lipids 22:207-220.
9. Gerson AR, Roberts KJ, Sherwood JN. 1991. X-ray powder diffraction studies of alkanes: unit-cell parameters of the homologous series C18H38 to C28H58. Acta Crystallogr Sect B Struct Sci B47(2):280-284.
10. Gil A, Ramirez M, Gil M. 2003. Role of long-chain polyunsaturated fatty acids in infant nutrition. Eur J Clin Nutr 57(Suppl 1):S31-S34.
11. Holman KT, Martin SM, Parker DP, Ward MD. 2001a. The generality of architectural isomerism in designer inclusion frameworks. J Am Chem Soc 123(19):4421-4431.
12. Holman KT, Pivovar AM, Swift JA, Ward MD. 2001b. Metric engineering of soft molecular host frameworks. Acc Chem Res 34(2):107-118.
13. Innis SM, Adamkin DH, Hall RT, Kalhan SC, Lair C, Lim M, Stevens DC, Twist PF, Diersen-Schade DA, Harris CL, et al. 2002. Docosahexaenoic acid and arachidonic acid enhance growth with no adverse effects in preterm infants fed formula. J Pediatrics (St. Louis, MO, United States) 140(5):547-554.
14. McNeill GP, Ackman RG, Moore SR. 1996. Lipase-catalyzed enrichment of long-chain polyunsaturated fatty acids. J Am Oil Chemists Soc 73(11):1403-1407.
15. Nikolova-Damyanova B. 2003. Lipid analysis by silver ion chromatography. Oily Press Lipid Library (advances in lipid methodology-five) 16 :43-123.
16. Pivovar AM, Holman KT, Ward MD. 2001. Shape-selective separation of molecular isomers with tunable hydrogen-bonded host frameworks. Chem Mater 13(9):3018-3031.
17. Polyakov NE, Leshina TV, Konovalova TA, Hand EO, Kispert LD. 2004. Inclusion complexes of carotenoids with cyclodextrins: 1H-NMR, EPR, and optical studies. Free Radic Biol Med 36(7):872-880.
18. Russell VA, Evans CC, Li W, Ward MD. 1997. Nanoporous molecular sandwiches: Pillared two-dimensional hydrogen-bonded networks with adjustable porosity. Science (Washington, D.C.) 276(5312):575-579.
19. Sada K, Inoue K, Tanaka T, Tanaka A, Epergyes A, Nagahama S, Matsumoto A, Miyata M. 2004. Organic layered crystals with adjustable interlayer distances of 1-naphthylmethylammonium n-alkanoates and isomerism of hydrogen-bond networks by steric dimension. J Am Chem Soc 126(6):1764-1771.
20. Schlenk H. 1961. Crystallization of fatty acids. J Am Oil Chemists Soc 38:728-736.
21. Schlenk H, Holman RT. 1950. Separation and stabilization of fatty acids by urea complexes. J Am Chem Soc 72:5001-5004.
22. Simopoulos AP. 1999. Essential fatty acids in health and chronic disease. Am J Clin Nutr 70(Suppl 3):560S-569S.
23. Sirish M, Schneider H-J. 2000. Highly Efficient complexations of a porphyrin dimer with remarkably small differences between nucleosides and nucleotides/the predominance of stacking interactions for nucleic acid components. J Am Chem Soc 122(24):5881-5882.
24. Teramoto M, Matsuyama H, Ohnishi N, Uwagawa S, Nakai K. 1994. Extraction of ethyl and methyl esters of polyunsaturated fatty acids with aqueous silver nitrate solutions. Ind Eng Chem Res 33(2):341-345.
25. Voogt JN, Blanch HW. 2005. Temperature-dependent solvent disruption of guanidinium-1,5-naphthalenedisulfonate networks yields a one-dimensional pore structure. Crystal Growth Design 5:1135-1144.