γ-Cyclodextrin: A review on enzymatic production and applications

Applied Microbiology and Biotechnology

Volumn 77, Issue 2, 2007, Pages 245-255

  Li, Zhaofeng ^a   Wang, Miao ^a   Wang, Feng ^a   Gu, Zhengbiao ^a   Du, Guocheng ^a   Wu, Jing ^a   Chen, Jian ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

Application; Cyclodextrin glycosyltransferase; Enzymatic production; Gamma Cyclodextrin; Property

Indexed keywords

BIOACTIVITY; CYCLODEXTRINS; DRUG PRODUCTS; STARCH;

APPLICATION; CYCLODEXTRIN GLYCOSYLTRANSFERASE; ENZYMATIC PRODUCTION; GAMMA-CYCLODEXTRIN; PROPERTY;

ENZYME ACTIVITY;

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CYCLOMALTODEXTRIN GLUCANOTRANSFERASE; DIGOXIN; GAMMA CYCLODEXTRIN; MICROCRYSTALLINE CELLULOSE; OMEPRAZOLE; OXAZEPAM; PACLITAXEL; PRAZIQUANTEL; SPIRONOLACTONE; UBIDECARENONE; WATER;

BIOAVAILABILITY; CARBOHYDRATE; ENZYME; SOLUBILITY; STARCH;

BIOAVAILABILITY; DRUG BIOAVAILABILITY; DRUG INDUSTRY; ENZYME SYNTHESIS; FOOD INDUSTRY; HUMAN; NONHUMAN; SHORT SURVEY; SOLUBILITY;

BACILLUS; GAMMA-CYCLODEXTRINS; GLUCOSYLTRANSFERASES; INDUSTRIAL MICROBIOLOGY;

EID: 35649000433     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-007-1166-7     Document Type: Short Survey

References (101)

1. Arias MJ, Moyano JR, Munoz P, Gines JM, Justo A, Giordano F (2000) Study of omeprazole-gamma-cyclodextrin complexation in the solid state. Drug Dev Ind Pharm 26:253-259
2. Bar R (1989) Cyclodextrin aided bioconversions and fermentations. Trends Biotechnol 7:2-4
3. Becket G, Schep LJ, Tan MY (1999) Improvement of the in vitro dissolution of praziquantal by complexation with alpha-, beta and gamma-cyclodextrins. Int J Pharm 179:65-71
4. Bender H (1983) An improved method for the preparation of cyclooctaamylose, using starches and the cyclodextrin glycosyltransferase of Klebsiella pneumoniae M 5 al. Carbohydr Res 124:225-233
5. Biwer A, Antranikian G, Heinzle E (2002) Enzymatic production of cyclodextrins. Appl Microbiol Biotechnol 59:609-617
6. Buschmann HJ, Schollmeyer E (2002) Applications of cyclodextrins in cosmetic products: a review. J Cosmet Sci 53:575-592
7. Buschmann HJ, Knittel D, Schollmeyer E (2001) New textile applications of cyclodextrins. J Incl Phenom Macrocycl Chem 40:169-172
8. Cao XZ, Jin ZY, Wang X, Chen F (2005) A novel cyclodextrin glycosyltransferase from an alkalophilic Bacillus species: purification and characterization. Food Res Int 38:309-314
9. Challa R, Ahuja A, Ali J, Khar RK (2005) Cyclodextrins in drug delivery: an updated review. AAPS PharmSciTech 6:E329-E357
10. 14C-gamma-cyclodextrin in germ-free and conventional rats. Regul Toxicol Pharmacol 27:150-158
11. Endo T, Zheng M, Zimmermann W (2002) Enzymatic synthesis and analysis of large-ring cyclodextrins. Aust J Chem 55:39-48
12. Englbrecht A, Harrer G, Lebert M (1988) Biochemical and genetic characterization of a CGTase from an alkalophilic bacterium forming primarily γ-cyclodextrin. In: Huber O, Szejtli J (eds) Proceedings of the fourth international symposium on cyclodextrins. Kluwer, Dordrecht, pp 87-92
13. Fava F, Gioia D, Marchetti L (1998) Cyclodextrin effects on the ex-situ bioremediation of a chronically polychlorobiphenyl-contaminated soil. Biotechnol Bioeng 58:345-55
14. Food Standards in Australia New Zealand (2003) Final assessment report, application a438: gamma cyclodextrin as a novel food ingredient/food additive. March 19
15. French D (1957) The Schardinger dextrins. Adv Carbohydr Chem 12:189-260
16. Friedman SH, Schinazi RF, Wudl F, Hill CL, DeCamp DL, Sijbesma RP, Kenyon GL (2003) Method of treatment of viral infection including hiv using water soluble fullerenes. US Patent 6613771
17. Fugita Y, Tsubouchi H, Inagi Y, Tomita K, Ozaki A, Nakanishi K (1990) Purification and properties of cyclodextrin glycosyltransferase from Bacillus sp. AL-6. J Ferment Bioeng 70:150-154
18. George B, Govindaraj M, Ujiie H, Freeman H, Hudson S (2004) Integration of fabric formation and coloration processes. NTC Research Briefs June:C02-PH03
19. Goel A, Nene S (1995) A novel cyclomaltodextrin glucanotransferase from Bacillus firmus that degrades raw starch. Biotechnol Lett 17:411-416
20. Han SM (1997) Direct enantiomeric separations by high performance liquid chromatography using cyclodextrins. Biomed Chromatogr 11:259-271
21. Harata K, Haga K, Nakamura A, Aoyagi M, Yamane M (1996) X-Ray structure of cyclodextrin glucanotransferase from alkalophilic Bacillus sp. 1011. Comparison of two independent molecules at 1.8 Å resolution. Acta Crystallogr D Biol Crystallogr 52:1136-1145
22. Hedges AR (1998) Industrial applications of cyclodextrins. Chem Rev 98:2035-2044
23. Hirano K, Ishihara T, Ogasawara S, Maeda H, Abe K, Nakajima T, Yamagata Y (2005) Molecular cloning and characterization of a novel γ-CGTase from alkalophilic Bacillus sp. Appl Microbiol Biotechnol 67:1-9
24. Irie T, Uekama K (1999) Cyclodextrins in peptide and protein delivery. Adv Drug Deliv Rev 36:101-123
25. Jarho P, Vander Velde D, Stella VJ (2000) Cyclodextrin-catalyzed deacetylation of spironolactone is pH and cyclodextrin dependent. J Pharm Sci 89:241-249
26. Kato T, Horikoshi K (1986) A new γ-cyclodextrin forming enzyme prodiced by Bacillus subtilis no. 313.. J Jpn Soc Starch Sci 34:137-143
27. Kim MH, Sohn CB, Oh TK (1998) Cloning and sequencing of a cyclodextrin glycosyltransferase gene from Brevibacillus brevis CD162 and its expression in Escherichia coli. FEMS Microbiol Lett 164:411-418
28. Komatsu K, Fujiwara K, Murata Y, Braun T (1999) Aqueous solubilization of crystalline fullerenes by supramolecular complexation with γ-cyclodextrin and sulfocalix under mechanochemical high speed vibration milling. J Chem Soc Perkin Trans 1:2963-2966
29. Kondo H, Nakatani H, Hiromi K (1990) In vitro action of human and porcine α-amylases on cyclo-maltooligosaccharides. Carbohydr Res 204:207-213
30. Koppenhoefer B, Epperlein U, Christian B, Ji Y, Chen Y, Lin B (1995) Separation of enantiomers of drugs by capillary electrophoresis: part I. Gamma-cyclodextrin as chiral solvating agent. J Chromatogr 717:181-190
31. Koppenhoefer B, Epperlein U, Jakob A, Wuerthner S, Zhu X, Lin B (1998) Separation of enantiomers of drugs by capillary electrophoresis, part 7: gamma-cyclodextrin as chiral solvating agent. Chirality 10:548-554
32. Lawson CL, van Montfort R, Strokopytov B, Rozeboom HJ, Kalk KH, de Vries GE, Penninga D, Dijkhuizen L, Dijkstra BW (1994) Nucleotide sequence and X-ray structure of cyclodextrin glycosyltransferase from Bacillus circulans strain 251 in a maltose-dependent crystal form. J Mol Biol 236:590-600
33. Lai CS, Chow JM, Wolf BW (2005) Method of using gamma cyclodextrin to control blood glucose and insulin secretion. US Patent 20050215523 A1
34. Lipman RD (2000) Cyclodextrin containing pressure sensitive adhesives. Eur Patent EP1206290
35. Loftsson T, Brewester M (1996) Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 85:1017-1025
36. Marshall JJ, Miwa I (1981) Kinetic difference between hydrolyses of γ-cyclodextrin by human salivary and pancreatic α-amylases. Biochim Biophys Acta 661:142-147
37. Martins RF, Hatii-Kaul R (2002) A new cyclodextrin glycosyltransferase from an alkaliphilic Bacillus agaradhaerens isolate: purification and characterization. Enzyme Microb Technol 30:116-124
38. Martin Del Valle EM (2004) Cyclodextrins and their uses: a review. Process Biochem 39:1033-1046
39. Matioli G, Zanin GM, Moraes FF (2000) Enhancement of selectiveity for producing γ-cyclodextrin. Appl Biochem Biotech 84-86:955-962
40. Matsuda H, Arima H (1999) Cyclodextrins in transdermal and rectaldelivery. Adv Drug Deliv Rev 36:81-99
41. McMahon WA, Lew CW, Branly KL (1995) Controlled release microcapsules. US Patent 5466460
42. Moldenhauer JP, Cully J (2003) Method for producing a coenzyme Q10/γ-cyclodextrin complex. US Patent 20030012774 A1
43. Moldenhauer JP, Regiert M, Wimmer T (1998) Complexes of gamma-cyclodextrin and retinol or retinol derivatives, processes for their preparation and their use. US Patent 5985296
44. Mori S, Hirose S, Oya T, Kitahata S (1994) Purification and properties of cyclodextrin glucanotransferase from Brevibacterium sp. No. 9605. Biosci Biotech Biochem 58:1968-1972
45. Moyano Mendez JR, Arias Blanco MJ, Gines Dorado JM, Rabasco Alvarez AM (1995) Application of γ-cyclodextrin to the improvement of dissolution characteristics of oxazepam. Il Farmaco 50:791-799
46. Munro IC, Newberne PM, Young VR, Bär A (2004) Safety assessment of γ-cyclodextrin. Regul Toxicol Pharm 39:S3-S13
47. Muoz-Botella S, del Castillo B, Martyn MA (1995) Cyclodetrin properties and applications of inclusion complex formation. Ars Pharm 36:187-198
48. Nakagawa Y, Takada M, Ogawa K, Hatada Y, Horikoshi K (2006) Site-directed mutations in Alanine 223 and Glycine 255 in the acceptor site of gamma-cyclodextrin glucanotransferase from Alkalophilic Bacillus clarkii 7364 affect cyclodextrin production. J Biochem (Tokyo) 140:329-336
49. O'Donnell CD (2001) New encapsulating molecule improves taste. prepared foods july from website: http://findarticles.com/p/articles/mi_m3289/is_7_170/ ai_77107380
50. Parsiegla G, Schmidt AK, Schulz GE (1998) Substrate binding to a cyclodextrin glycosyltransferase and mutations increasing the γ-cyclodextrin production. Eur J Biochem 255:710-717
51. Penninga D, Strokopytov B, Rozeboom HJ, Lawson CL, Dijkstra BW, Bergsma J, Dijkhuizen L (1995) Site directed mutations in tyrosine 195 of cyclodextrin glycosyltransferase from Bacillus circulans strain 251 affect activity and product specificity. Biochemistry 34:3368-3376
52. Prabhu KS, Ramadoss CS (2000) Penicillin acylase catalyzed synthesis of penicillin-G from substrates anchored in cyclodextrins. Indian J Biochem Biophys 37:6-12
53. Qi Q, Zimmermann W (2005) Cyclodextrin glucanotransferase: from gene to applications. Appl Microbiol Biotechnol 66:475-485
54. Qi Q, Mokhtar MN, Zimmermann W (2007) Effect of ethanol on the synthesis of large-ring cyclodextrins by cyclodextrin glucanotransferases. J Incl Phenom Macrocycl Chem 57:95-99
55. Rajewski RA, Stella VJ (1996) Pharmaceutical applications of cyclodextrins.2. In vivo drug delivery. J Pharm Sci 85:1142-68
56. Redenti E, Fronza G, Bovis G, Ventura P (1992) Application of γ-cyclodextrin to enantiomeric purity determination of a new 2-amino-tetralin derivative by H-1-NMR spectroscopy. Chirality 4:404-405
57. Regiert M (2005) Light-stable vitamin E by inclusion in gamma-cyclodextrin. SOEFW Int J Appl Sci 131:10-18
58. Regiert M, Kupka M (2003) 2:1-Inclusion compound from beta- or gamma-cyclodextrin and alpha-tocopherol. US Patent 20030130231A1
59. Regiert M, Kupka M (2004) Cosmetic composition comprising a complex of cyclodextrin and vitamin F. US Patent 20040096413 A1
60. Regiert M, Moldenhauer JP (1998) Inclusion compound from gamma-cyclodextrin and retinol, production and application. Eur Patent EP0867175 A1, DE19847633 C1
61. Regiert M, Wimmer T, Moldenhauer JP (1996) Application of γ-cyclodextrin for the stabilization and/or dispersion of vegetable oils containing triglycerides of polyunsaturated acids. J Inclu Pheno Mol Recogn Chem 25:213-216
62. 12 cyclic compounds. Carbohyd Res 230:343-359
63. Rendleman JA Jr (1993) Enhanced production of γ-cyclodextrin from corn syrup solids by means of cyclododecanone as selective complexant. Carbohydr Res 247:223-237
64. Rosenfeldt F, Hilton D, Pepe S, Krum H (2003) Systematic review of effect of coenzyme Q10 in physical exercise, hypertension and heart failure. Biofactors 18:91-100
65. Rusa CC, Rusa M, Gomez M, Shin I, Fox J, Tonelli AE (2004) Nanostructuring high molecular weight isotactic polyolefins via processing with γ-cyclodextrin inclusion compounds. formation and characterization of polyolefin- γ-cyclodextrin inclusion compounds. Macromolecules 37:7992-7999
66. Sato M, Yagi Y (1991) Properties of CGTase from three types of Bacillus and production of cyclodextrins by the enzymes. In: Friedman RB (ed) Biotechnology of amylodextrin oligosaccharides, ACS symposium series 458. American Chemical Society, Washington, DC, pp 125-137
67. Schmid G (1996) Preparation and industrial production of cyclodextrins. In: Atwood J, Davies ED, MacNicol DD, Vogtle F (eds) Comprehesive supermolecular chemistry, vol 3: Cyclodextrins. Pergamon, Oxford, pp 41-56
68. Schneiderman E, Stalcup AM (2000) Cyclodextrins: a versatile tool in separation science. J Chromatogr B 745:83-102
69. Shieh W (1996) Process for producing gamma-cyclodextrin. US Patent 5550222
70. Singla AK, Garg A, Aggarwal D (2002) Paclitaxel and its formulations. Int J Pharm 235:179-192
71. Strokopytov B, Knegtel RM, Penninga D, Rozeboom HJ, Kalk KH, Dijkhuizen L, Dijkstra BW (1996) Structure of cyclodextrin glycosyltransferase complexed with a maltononaose inhibitor at 2.6 angstrom resolution. Implications for product specificity. Biochemistry 35:4241-4249
72. 70 compounds. Chem Phys Lett 344:263-269
73. Szejtli J (1982) Cyclodextrins and their inclusion complexes. Akademiai Kiado, Budapest
74. Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98:1743-1753
75. Szejtli J (2003) Cyclodextrins in the textile industry. Starch/Stärke 55:191-196
76. Szejtli J (2004) Past, present, and future of cyclodextrin research. Pure Appl Chem 76:1825-1845
77. Szente L, Szejtli J (2004) Cyclodextrins as food ingredients. Trends Food Sci Tech 15:137-142
78. Takada M, Ide T, Yamamoto T, Unno T, Watanabe Y, Sone H, Yamamoto M (2003a) Novel cyclodextrin glucanotransferase, process for producing the same and process for producing cyclodextrin by using this enzyme. US Patent 20030194796 A1
79. Takada M, Nakagawa Y, Yamamoto T (2003b) Biochemical and genetic analyses of a novel γ-cyclodextrin glucanotransferase from an alkalophilic Bacillus clarkii 7364. J Biochem (Tokyo) 133:317-324
80. Tamura H, Takada M, Shiomi K (1999) The color stability and antioxidative activity of an anthocyanin and γ-cyclodextrin complex. In: Shibamoto T, Terao J, Osawa T (eds) Functional foods for disease prevention 1: fruits, vegetables, and teas, ACS symposium series 701. American Chemical Society, Washington, DC, pp 157-171
81. Terada Y, Yanase M, Takata H, Takaha T, Okada S (1997) Cyclodextrins are not the major cyclic α-1,4-glucans produced by the initial action of cyclodextrin glucanotransferase on amylose. J Biol Chem 272:15729-15733
82. 10 by complexation with γ-cyclodextrin in healthy adults. Nutr Res 26:503-508
83. Thoss M, Schwabe L, Fromming KH (1993) Cyclodextrin- Einschlussverbindungen von Zitronen-, Orangen-, Hopfen- und Kamillenol. Pharm Ztg Wiss 6:144-148
84. Tonkova A (1998) Bacterial cyclodextrin glucanotransferase. Enzyme Micro Technol 22:678-686
85. Uchiyama H, Jensen JM, DuVal DL, Cetti JR, Woo RA, Archambault DL (2002) Reduction of odors from coating material. US Patent 20020132861 A1
86. Uekama K, Fujinaga T, Hirayama F, Otagiri M, Yamasaki M, Seo H, Hashimoto T, Tsuruoka M (1983) Improvement of the oral bioavailability of digitalis glycosides by cyclodextrin complexation. J Pharm Sci 72:1338-1341
87. Uitdehaag JC, Mosi R, Kalk KH, van der Veen BA, Dijkhuizen L, Withers SG, Dijkstra BW (1999a) X-Ray structures along the reaction pathway of cyclodextrin glycosyltransferase elucidate catalysis in the α-amylase family. Nat Struct Biol 6:432-436
88. Uitdehaag JC, Kalk KH, van Der Veen BA, Dijkhuizen L, Dijkstra BW (1999b) The cyclization mechanism of cyclodextrin glycosyltransferase (CGTase) as revealed by a γ-cyclodextrin-CGTase complex at 1.8-A resolution. J Biol Chem 274:34868-34876
89. Uitdehaag JC, van Alebeek GJ, van Der Veen BA, Dijkhuizen L, Dijkstra BW (2000a) Structures of maltohexaose and maltoheptaose bound at the donor sites of cyclodextrin glycosyltransferase give insight into the mechanisms of transglycosylation activity and cyclodextrin size specificity. Biochemistry 39:7772-7780
90. Uitdehaag JC, van der Veen BA, Dijkhuizen L, Dijkstra BW (2000b) Catalytic mechanism and product specificity of cyclodextrin glycosyltransferase, a prototypical transglycosylase from the α-amylase family. Enzyme Microb Technol 30:295-304
91. van der Veen BA, Uitdehaag JC, Dijkstra BW, Dijkhuizen L (2000a) Engineering of cyclodextrin glycosyltransferase reaction and product specificity. Biochim Biophys Acta 1543:336-360
92. van der Veen BA, van Alebeek GJ, Uitdehaag JC, Dijkstra BW, Dijkhuizen L (2000b) The three transglycosylation reactions catalyzed by cyclodextrin glycosyltransferase from Bacillus circulans (strain 251) proceed via different kinetic mechanisms. Eur J Biochem 267:658-665
93. van der Veen BA, Uitdehaag JC, Dijkstra BW, Dijkhuizen L (2000c) The role of arginine 47 in the cyclization and coupling reactions of cyclodextrin glycosyltransferase from Bacillus circulans strain 251. Implications for product inhibition and product specificity. Eur J Biochem 267:3432-3441
94. Waalkens-Berendsen DH, Smits-van Prooije AE, Bär A (1998a) Embryotoxicity and teratogenicity study with γ-cyclodextrin in rabbits. Regul Toxicol Pharmacol 27:172-177
95. Waalkens-Berendsen DH, Verhagen FJ, Bär A (1998b) Embryotoxicity and teratogenicity study with γ-cyclodextrin in rats. Regul Toxicol Pharmacol 27:166-171
96. Wang F, Du GC, Li Y, Chen J (2004) Optimization of cultivation conditions for the production of γ-Cyclodextrin Glucanotranferase by Bacillus macorous. Food Biotechnol 18:251-264
97. Wang F, Du GC, Li Y, Chen J (2005) Effects of dissolved oxygen tension and two-stage oxygen supply strategy on the production of γ-CGTase by Bacillus macorous. Process Biochem 40:3468-3473
98. Wang F, Du GC, Li Y, Chen J (2006a) Regulation of CCR in the γ-CGTase production from Bacillus macorous by the specific cell growth rate control. Enzyme Microb Technol 39:1279-1285
99. Wang F, Du GC, Li Y, Chen J (2006b) Enhanced γ-CGTase production by Bacillus Macorous with membrane active substances. Food Biotechnol 20:171-181
100. Yang GW, Li J, Xie WM, Wang DM, Xie BT (2001) Studys on γ-CGTase from Bacillus sp. 32-3-1. Ind microbiol 31:30-32 (In Chinese)
101. Zheng M, Endo T, Zimmermann W (2002) Synthesis of large-ring cyclodextrins by cyclodextrin glucanotransferases from bacterial isolates. J Incl Phenom Macrocycl Chem 44:387-390