Cloning and functional characterization of the UDP-glucosyltransferase UgtB1 involved in sophorolipid production by Candida bombicola and creation of a glucolipid-producing yeast strain

Yeast

Volumn 28, Issue 4, 2011, Pages 279-292

  Saerens, Karen M J ^a   Zhang, Jinxin ^a   Saey, Lien ^a   Van Bogaert, Inge N A ^a   Soetaert, Wim ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Biosurfactant; Candida bombicola; Glucolipid; Glucosyltransferase; Sophorolipid

Indexed keywords

BACTERIAL ENZYME; BIOSURFACTANT; CARBAZOLE DERIVATIVE; GLUCOLIPID; GLUCURONOSYLTRANSFERASE; GLYCOLIPID; GLYCOSYLTRANSFERASE; INDOLOCARBAZOLE; LIPID; MACROLIDE; RIFAMYCIN; SOPHOROLIPID; STAUROSPORINE; UNCLASSIFIED DRUG;

ACTINOMADURA; ACTINOMADURA MELLIAURA; ARTICLE; CANDIDA; CANDIDA BOMBICOLA; CELL GROWTH; CELL LYSATE; FUNGAL GENE; FUNGAL STRAIN; GENE DELETION; GENE SEQUENCE; GLYCOSYLATION; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SEQUENCE HOMOLOGY; STREPTOMYCES; STREPTOMYCES CLAVULIGERUS; STRUCTURAL HOMOLOGY;

AMINO ACID SEQUENCE; BASE SEQUENCE; CANDIDA; CLONING, MOLECULAR; FUNGAL PROTEINS; GLUCOSYLTRANSFERASES; GLYCOLIPIDS; MOLECULAR SEQUENCE DATA; SEQUENCE ALIGNMENT; URIDINE DIPHOSPHATE;

BACTERIA (MICROORGANISMS); STARMERELLA BOMBICOLA;

EID: 79953289174     PISSN: 0749503X     EISSN: 10970061     Source Type: Journal    
DOI: 10.1002/yea.1838     Document Type: Article

References (60)

1. Abalos A, Pinazo A, Infante MR, et al. 2001. Physicochemical and antimicrobial properties of new rhamnolipids produced by Pseudomonas aeruginosa AT10 from soybean oil refinery wastes. Langmuir 17: 1367-1371.
2. Altschul SF, Madden TL, Schaffer AA, et al. 1997. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res 25: 3389-3402.
3. Banat IM, Franzetti A, Gandolfi I, et al. 2010. Microbial biosurfactants production, applications and future potential. Appl Microbiol Biotechnol 87: 427-444.
4. Basehoar AD, Zanton SJ, Pugh F. 2004. Identification and distinct regulation of yeast TATA box-containing genes. Cell 116: 699-709.
5. Bisht KS, Gross RA, Kaplan DL. 1999. Enzyme-mediated regioselective acylations of sophorolipids. J Org Chem 64: 780-789.
6. Bluth MH, Kandil E, Mueller CM, et al. 2006. Sophorolipids block lethal effects of septic shock in rats in a cecal ligation and puncture model of experimental sepsis. Crit Care Med 34: 250-259.
7. Brakemeier A, Wullbrandt D, Lang S. 1998. Candida bombicola: production of novel alkyl glycosides based on glucose/2-dodecanol. Appl Microbiol Biotechnol 50: 161-166.
8. Breithaupt TB, Light RJ. 1982. Affinity chromatography and further characterization of the glucosyltransferases involved in hydroxydocosanoic acid sophoroside production in Candida bogoriensis. J Biol Chem 257: 9622-9628.
9. Breton C, Snajdrova L, Jeanneau C, et al. 2006. Structures and mechanisms of glycosyltransferases. Glycobiology 16: 29-37.
10. Bucholtz ML, Light RJ. 1976. Acetylation of 13-sophorosyloxydocosanoic acid by an acetyltransferase purified from Candida bogoriensis. J Biol Chem 251: 424-430.
11. Campbell JA, Davies GJ, Vulone V, Henrissat B. 1997. A classification of nucleotide-diphospho-sugar glycosyltransferases based on amino acid sequence similarities. Biochem J 326: 929-942.
12. Carr JA, Bisht KS. 2003. Enzyme-catalyzed regioselective transesterification of peracylated sophorolipids. Tetrahedron 59: 7713-7724.
13. Chiu HT, Chen YL, Chen CY, et al. 2009. Molecular cloning, sequence analysis and functional characterization of the gene cluster for biosynthesis of K-252a and its analogs. Mol Biosyst 5: 1180-1191.
14. Coutinho PM, Deleury E, Davies GJ, Henrissat B. 2003. An evolving hierarchical family classification for glycosyltransferases. J Mol Biol 328: 307-317.
15. Davila AM, Marchal R, Vandecasteele JP. 1992. Kinetics and balance of a fermentation free from product inhibition-sophorose lipid production by Candida bombicola. Appl Microbiol Biotechnol 38: 6-11.
16. Dogan I, Pagilla KR, Webster DA, Startk BC. 2006. Expression of Vitreoscilla hemoglobin in Gordonia amarae enhances biosurfactant production. J Ind Microbiol Biotechnol 33: 693-700.
17. Esders TW, Light RJ. 1972. Glucosyl- and acetyltransferases involved in the biosynthesis of glycolipids from Candida bogoriensis. J Biol Chem 247: 1375-1386.
18. Franzetti A, Tamburini E, Banat IM. 2010. Applications of biological surface active compounds in remediation technologies. In Advances in Experimental Medicine and Biology, vol 672, Ramkrishna S (ed.). Springer-Verlag: Berlin; 121-134.
19. Fu SL, Wallner SR, Bowne WB, et al. 2008. Sophorolipids and their derivatives are lethal against human pancreatic cancer cells. J Surg Res 148: 77-82.
20. Gao Q, Zhang C, Blanchard S, Thorson JS. 2006. Deciphering indolocarbazole and enediyne aminodideoxypentose biosynthesis through comparative genomics: insights from the AT2433 biosynthetic locus. Chem Biol 13: 733-743.
21. Gietz RD, Schiestl RH. 1995. Transforming yeast with DNA. Methods Mol Cell Biol 5: 255-269.
22. Gross R, Shah V. 2004. Antimicrobial properties of various forms of sophorolipids. International Patent No. WO 2004/044216 A1.
23. Gross R, Shah V. 2005. Antifungal properties of various forms of sophorolipids US Patent No. 2005/0164955 A1.
24. Guo Z, Sherman F. 1996. Signals sufficient for 3'-end formation of yeast mRNA. Mol Cel Biol 16: 2772-2776.
25. Hall TA. 1999. BioEdit: a user-friendly biological sequence alignment editor and analysis program for windows 95/98/NT. Nucl Acids Symp Ser 41: 95-98.
26. Hewald S, Josephs K, Bölker M. 2005. Genetic analysis of biosurfactant production in Ustilago maydis. Appl Env Microbiol 71: 3033-3040.
27. Hewald S, Linne U, Scherer M, et al. 2006. Identification of a gene cluster for biosynthesis of mannosylerythritol lipids in the basidiomycetous fungus Ustilago maydis. Appl Environ Micr 72: 5469-5477.
28. Imura T, Masuda Y, Minamikawa H, et al. 2010. Enzymatic conversion of diacetylated sophoroselipid into acetylated glucoselipid: surface-active properties of novel bolaform biosurfactants. J Oleo Sci 59: 495-501.
29. Iqbal S, Khalid ZM, Malik KA. 1995. Enhanced biodegradation and emulsification of crude oil and hyperproduction of biosurfactants by a γ-ray-induced mutant of Pseudomonas aeruginosa. Lett Appl Microbiol 21: 176-179.
30. Kim SY, Park JS, Chae CS, et al. 2007. Genetic organization of the biosynthetic gene cluster for the indolocarbazole K-252a in Nonomuraea longicatena JCM 11136. Appl Microbiol Biotechnol 75: 1119-1126.
31. Kitamoto D, Yanagishita H, Shinbo T, et al. 1993. Surface-active properties and antimicrobial activities of mannosylerythritol lipids as biosurfactants produced by Candida antarctica. J Biotechnol 29: 91-96.
32. Koch AK, Kappeli O, Fiechter A, Reiser J. 1991. Hydrocarbon assimilation and biosurfactant production in Pseudomonas aeruginosa mutants. J Bacteriol 173: 4212-4219.
33. Kralova I, Sjoblom J. 2009. Surfactants used in food industry: a review. J Disper Sci Technol 30: 1363-1383.
34. Kulakovskaya EV, Kulakovskaya TV, Golubev VI, et al. 2007. Fungicidal activity of cellobiose lipids from culture broth of yeast Cryptococcus humicola and Pseudozyma fusiformata. Bioorg Khim 33: 167-171.
35. Lang S, Brakemeier A, Heckmann R, et al. 2000. Production of native and modified sophorose lipids. Chim Oggi 18: 76-79.
36. Magasanik B, Kaiser CA. 2002. Nitrogen regulation in Saccharomyces cerevisiae. Gene 290: 1-18.
37. Marchler-Bauer A, Anderson JB, Chitsaz F, et al. 2009. CDD: Specific functional annotation with the Conserved Domain Database. Nucleic Acids Res 37: 205-210.
38. Marzluf GA. 1997. Genetic regulation of nitrogen metabolism in the fungi. Micr Mol Biol Rev 61: 17-32.
39. Medema MH, Trefzer A, Kovalchuk A, et al. 2010. The sequence of a 1.8 Mb bacterial linear plasmid reveals a rich evolutionary reservoir of secondary metabolic pathways. Genome Biol Evol 2: 212-224.
40. Mimee B, Pelletier R, Bélanger RR. 2009. In vitro antibacterial activity and antifungal mode of action of flocculosin, a membrane-active cellobiose lipid. J Appl Microbiol 107: 989-996.
41. Mulligan CN. 2009. Recent advances in the environmental applications of biosurfactants. Curr Opin Colloid 14: 372-378.
42. Ochsner UA, Fiechter A, Reiser J. 1994. Isolation, characterization, and expression in Escherichia coli of the Pseudomonas aeruginosa rhlAB genes encoding a rhamnosyltransferase involved in rhamnolipid biosurfactant synthesis. J Biol Chem 269: 19787-19795.
43. Ochsner UA, Reiser J, Fiechter A, Witholt B. 1995. Production of Pseudomonas aeruginosa rhamnolipid biosurfactants in heterologous hosts. Appl Env Microbiol 61: 3503-3506.
44. Ohuchi T, Ikeda-Araki A, Watanabe-Sakamoto A, et al. 2000. Cloning and expression of a gene encoding N-glycosyltransferase (ngt) from Saccharothrix aerocolonigenes ATCC 39243. J Antibiot 53: 393-403.
45. Onaka H, Taniguchi S, Igarashi Y, Furumai T. 2002. Cloning of the staurosporine biosynthetic gene cluster from Streptomyces sp. TP-A0274 and its heterologous expression in Streptomyces lividans. J Antibiot 55: 1063-1071.
46. Palme O, Comanescu G, Stoineva I, et al. 2010. Sophorolipids from Candida bombicola: cell separation by ultrasonic particle manipulation. Eur J Lipid Sci Technol 112: 663-673.
47. Rau U, Hammen S, Heckmann R, et al. 2001. Sophorolipids: a source for novel compounds. Ind Crop Prod 13: 85-92.
48. Rau U, Heckmann R, Wray V, Lang S. 1999. Enzymatic conversion of a sophorolipid into a glucose lipid. Biotechnol Lett 21: 973-977.
49. Rodrigues LR, Teixeira JA. 2010. Biomedical and therapeutic applications of biosurfactants. In Advances in Experimental Medicine and Biology, vol 672, Ramkrishna S. (ed.). Springer-Verlag: Berlin; 75-87.
50. Saerens KMJ, Roelants SLKW, Van Bogaert INA, Soetaert W. In press. Identification of the UDP-glucosyltransferase gene UGTA1, responsible for the first glucosylation step in the sophorolipid biosynthetic pathway of Candida bombicola ATCC 22214. FEMS Yeast Res DOI: 10.1111/j.1567-1364.2010.00695.x.
51. Saerens K, Van Bogaert I, Soetaert W, Vandamme E. 2009. Production of glucolipids and specialty fatty acids from sophorolipids by Penicillium decumbens naringinase: optimization and kinetics. Biotechnol J 4: 517-524.
52. Sambrook J, Russell, DW. 2001. Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY.
53. Shah V, Doncel GF, Seyoum T, et al. 2005. Sophorolipids, microbial glycolipids with anti-human immunodeficiency virus and sperm-immobilizing activities. Antimicrob Agents Chemother 49: 4093-4100.
54. Teichmann B, Linne U, Hewald S, et al. 2007. A biosynthetic gene cluster for a secreted cellobiose lipid with antifungal activity from Ustilago maydis. Mol Microbiol 66: 525-533.
55. Teichmann B, Liu L, Schink KO, Bölker M. 2010. Activation of the ustilagic acid biosynthesis gene cluster in Ustilago maydis by the C2H2 zinc finger transcription factor Rua1. Appl Env Microbiol 76: 2633-2640.
56. Vakil H, Sethi S, Fu S, et al. 2010. Sophorolipids decrease pulmonary inflammation in a mouse asthma model. Mod Pathol 23: 392A.
57. Van Bogaert INA, De Maeseneire SL, Develter D, et al. 2008. Development of a transformation and selection system for the glycolipid producing yeast Candida bombicola. Yeast 25: 272-278.
58. Van Bogaert INA, De Mey M, Develter D, et al. 2009. Importance of the cytochrome P450 monooxygenase CYP52 family for the sophorolipid-producing yeast Candida bombicola. FEMS Yeast Res 9: 87-94.
59. Zhao W, Zhong Y, Yuan H, et al. 2010. (in press). Complete genome sequence of the rifamycin SV-producing Amycolatopsis mediterranei U32 revealed its genetic characteristics in phylogeny and metabolism. Cell Res: doi:10.1038/cr.2010.87.
60. Zhou SQ, Xu C, Wang J, et al. 2004. Supramolecular assemblies of a naturally derived sophorolipid. Langmuir 20: 7926-7932.