Elucidation of first step of the allylmalonyl-CoA biosynthetic pathway by expression of heterologous KSIII gene and enhancement of 36-methyl-FK506 production by genetic and chemical engineering
详细信息    查看全文
  • 作者：SangJoon Mo ; Joo-Won Suh
  • 关键词：36 ; Methyl ; FK506 ; Allylmalonyl ; CoA ; β ; Ketoacyl ; acyl carrier protein synthase III ; FK506 ; Heterologous expression
  • 刊名：Journal of the Korean Society for Applied Biological Chemistry
  • 出版年：2016
  • 出版时间：February 2016
  • 年：2016
  • 卷：59
  • 期：1
  • 页码：77-88
  • 全文大小：1,767 KB
  • 参考文献：Aldape RA, Futer O, DeCenzo MT, Jarrett BP, Murcko MA, Livingston DJ (1992) Charged surface residues of FKBP12 participate in formation of the FKBP12-FK506-calcineurin complex. J Biol Chem 267:16029–16032
    Bao W, Sheldon PJ, Hutchinson CR (1999a) Purification and properties of the Streptomyces peucetius DpsC beta-ketoacyl:acyl carrier protein synthase III that specifies the propionate-starter unit for type II polyketide biosynthesis. Biochemistry 38:9752–9757CrossRef
    Bao W, Sheldon PJ, Wendt-Pienkowski E, Hutchinson CR (1999b) The Streptomyces peucetius dpsC gene determines the choice of starter unit in biosynthesis of the daunorubicin polyketide. J Bacteriol 181:4690–4695
    Dumont FJ (2000) FK506, an immunosuppressant targeting calcineurin function. Curr Med Chem 7:731–748CrossRef
    Eustáquio AS, McGlinchey RP, Liu Y, Hazzard C, Beer LL, Florova G, Alhamadsheh MM, Lechner A, Kale AJ, Kobayashi Y, Reynolds KA, Moore BS (2009) Biosynthesis of the salinosporamide A polyketide synthase substrate chloroethylmalonyl-coenzyme A from S-adenosyl-L-methionine. Proc Natl Acad Sci USA 106:12295–12300CrossRef
    Goranovič D, Kosec G, Mrak P, Fujs S, Horvat J, Kuščer E, Kopitar G, Petković H (2010) Origin of the allyl group in FK506 biosynthesis. J Biol Chem 285:14292–14300CrossRef
    Haddad EM, McAlister VC, Renouf E, Malthaner R, Kjaer MS, Gluud LL (2006) Cyclosporin versus tacrolimus for liver transplanted patients. Cochrane Database Syst Rev 18(4):CD005161
    Kieser T, Bibb MJ, Buttner MJ, Chater KF, Hopwood DA (2000) Practical Streptomyces genetics. John Innes Foundation, Norwich
    Kino T, Hatanaka H, Hashimoto M, Nishiyama M, Goto T, Okuhara M, Kohsaka M, Aoki H, Imanaka H (1987a) FK-506, a novel immunosuppressant isolated from a Streptomyces. I. Fermentation, isolation, and physico-chemical and biological characteristics. J Antibiot (Tokyo) 40:1249–1255CrossRef
    Kino T, Hatanaka H, Miyata S, Inamura N, Nishiyama M, Yajima T, Goto T, Okuhara M, Kohsaka M, Aoki H, Ochiai T (1987b) FK-506, a novel immunosuppressant isolated from a Streptomyces. II. Immunosuppressive effect of FK-506 in vitro. J Antibiot (Tokyo) 40:1256–1265CrossRef
    Klettner A, Herdegen T (2003) FK506 and its analogs—therapeutic potential for neurological disorders. Curr Drug Targets CNS Neurol Disord 2:153–162CrossRef
    Kumar P, Malviya HK, Maurya RK, Shukla A (2007) Fermentation processes for the preparation of tacrolimus. International publication patent no. WO2007/039816 A2
    Lechner A, Wilson MC, Ban YH, Hwang JY, Yoon YJ, Moore BS (2013) Designed biosynthesis of 36-methyl-FK506 by polyketide precursor pathway engineering. ACS Synth Biol 2:379–383CrossRef
    Lee SK, Yang SH, Kang CM, Mo S, Suh JW (2014) Overexpression of the putative extracytoplasmic function sigma (σ) factor FujE enhances FK506 production in Streptomyces sp. strain KCCM 11116P. Can J Microbiol 60:363–369CrossRef
    Lin AN (2010) Innovative use of topical calcineurin inhibitors. Dermatol Clin 28:535–545CrossRef
    Liu J, Farmer JD Jr, Lane WS, Friedman J, Weissman I, Schreiber SL (1991) Calcineurin is a common target of cyclophilin-cyclosporin A and FKBP-FK506 complexes. Cell 66:807–815CrossRef
    Liu Y, Hazzard C, Eustáquio AS, Reynolds KA, Moore BS (2009) Biosynthesis of salinosporamides from α, β -unsaturated fatty acids: implications for extending polyketide synthase diversity. J Am Chem Soc 131:10376–10377CrossRef
    Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR (1999) Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J Bacteriol 181:305–318
    Martínez-Castro M, Salehi-Najafabadi Z, Romero F, Pérez-Sanchiz R, Fernández-Chimeno RI, Martín JF, Barreiro C (2013) Taxonomy and chemically semi-defined media for the analysis of the tacrolimus producer ‘Streptomyces tsukubaensis’. Appl Microbiol Biotechnol 97:2139–2152CrossRef
    Meier-Kriesche HU, Chu AH, David KM, Chi-Burris K, Steffen BJ (2006) Switching immunosuppression medications after renal transplantation–a common practice. Nephrol Dial Transplant 21:2256–2262CrossRef
    Mo S, Kim BS, Reynolds KA (2005) Production of branched-chain alkylprodiginines in S. coelicolor by replacement of the 3-ketoacyl ACP synthase III initiation enzyme. RedP. Chem Biol 12:191–200CrossRef
    Mo S, Ban YH, Park JW, Yoo YJ, Yoon YJ (2009) Enhanced FK506 production in Streptomyces clavuligerus CKD1119 by engineering the supply of methylmalonyl-CoA precursor. J Ind Microbiol Biotechnol 36:1473–1482CrossRef
    Mo S, Kim DH, Lee JH, Park JW, Basnet DB, Ban YH, Yoo YJ, Chen SW, Park SR, Choi EA, Kim E, Jin YY, Lee SK, Park JY, Liu Y, Lee MO, Lee KS, Kim SJ, Kim D, Park BC, Lee SG, Kwon HJ, Suh JW, Moore BS, Lim SK, Yoon YJ (2011) Biosynthesis of the allylmalonyl-CoA extender unit for the FK506 polyketide synthase proceeds through a dedicated polyketide synthase and facilitates the mutasynthesis of analogues. J Am Chem Soc 133:976–985CrossRef
    Mo S, Lee SK, Jin YY, Oh CH, Suh JW (2013) Application of a combined approach involving classical random mutagenesis and metabolic engineering to enhance FK506 production in Streptomyces sp. RM7011. Appl Microbiol Biotechnol 97:3053–3062CrossRef
    Motamedi H, Shafiee A (1998) The biosynthetic gene cluster for the macrolactone ring of the immunosuppressant FK506. Eur J Biochem 256:528–534CrossRef
    Park JW, Mo SJ, Park SR, Ban YH, Yoo YJ, Yoon YJ (2009) Liquid chromatography-mass spectrometry characterization of FK506 biosynthetic intermediates in Streptomyces clavuligerus KCTC 10561BP. Anal Biochem 393:1–7CrossRef
    Periyasamy S, Warrier M, Tillekeratne MP, Shou W, Sanchez ER (2007) The immunophilin ligands cyclosporin A and FK506 suppress prostate cancer cell growth by androgen receptor-dependent and -independent mechanisms. Endocrinology 148:4716–4726CrossRef
    Quade N, Huo L, Rachid S, Heinz DW, Müller R (2011) Unusual carbon fixation gives rise to diverse polyketide extender units. Nat Chem Biol 8:117–124CrossRef
    Rath T (2013) Tacrolimus in transplant rejection. Expert Opin Pharmacother 14:115–122CrossRef
    Remitz A, Reitamo S (2009) Long-term safety of tacrolimus ointment in atopic dermatitis. Expert Opin Drug Saf 8:501–506CrossRef
    Sambrook J, Russell DW (2001) Molecular cloning: a laboratory manual, 3rd edn. Cold Spring Harbor, New York
    Schreiber SL, Crabtree GR (1992) The mechanism of action of cyclosporin A and FK506. Immunol Today 13:136–142CrossRef
    Smirnova N, Reynolds KA (2001) Branched-chain fatty acid biosynthesis in Escherichia coli. J Ind Microbiol Biotechnol 27:246–251CrossRef
    Trede NS, Warwick AB, Rosoff PM, Rohrer R, Bierer BE, Guinan E (1997) Tacrolimus (FK506) in allogeneic bone marrow transplantation for severe aplastic anemia following orthotopic liver transplantation. Bone Marrow Transplant 20:257–260CrossRef
    Webster A, Woodroffe RC, Taylor RS, Chapman JR, Craig JC (2005) Tacrolimus versus cyclosporin as primary immunosuppression for kidney transplant recipients. Cochrane Database Syst Rev 41(4):CD003961
    Wu K, Chung L, Revill WP, Katz L, Reeves CD (2000) The FK520 gene cluster of Streptomyces hygroscopicus var. ascomyceticus (ATCC 14891) contains genes for biosynthesis of unusual polyketide extender units. Gene 251:81–90CrossRef
  • 作者单位：SangJoon Mo (2)
    Joo-Won Suh (1)

    2. Biosafety & Validation Center, Clinical Trial Institute, Dankook University, Choenan, 330-714, Chungnam, Republic of Korea
    1. Department of Biological Science, Institute of Bioscience and Biotechnology, Myongji University, Yongin, 449-728, Gyeonggi-Do, Republic of Korea
  • 刊物主题：Applied Microbiology; Bioorganic Chemistry; Biological Techniques;
  • 出版者：Springer Netherlands
  • ISSN：2234-344X
文摘
We identified another tcsABCD genes encoding biosynthesis of the allylmalonyl-CoA in new FK506 producing strain, Streptomyces sp. KCCM 11116P. The functionality of tcsABCD is confirmed by gene deletion. To validate the functionality of these genes, tcsABCD genes were heterologously expressed in Streptomyces hygroscopicus ATCC 14891 using pSE34. The resulting strain produced the FK506 which showed a molecular ion [M+NH4]+ at m/z 821 as verified by LC/ESI–MS. To address the function of TcsB in the allylmalonyl-CoA pathway, we pursued the construction of two different combinations: the heterologous FabH-like β-ketoacyl-acyl carrier protein synthase III gene expression and chemical complementation. Plasmid-based expression of the fabH homolog dpsC in ΔTcsB using pSE34 and pSET152(ermE*) led to restoration of approximately 32.2 and 28.7 % of the levels of FK506 relative to Streptomyces sp. KCCM 11116P, respectively. Furthermore, the addition of propionic acid to the culture of ΔTcsB restored FK506 production up to 35.6 % of overall FK506 levels in Streptomyces sp. KCCM 11116P. We have engineered production of 36-methyl-FK506 in ΔTcsB. The heterologous expression of Syteptomyces glaucescens FabH in ΔTcsB gave rise to 5.9-fold increase in the 36-methyl-FK506 level as compared with mutasynthetic production by 4-methylpentanoic acid. Supplementing the culture broth of ΔTcsB expressing S. glaucescens FabH with valine resulted in an additional 2.5-fold increase in the 36-methyl-FK506 titer. Overall, this study shows that TcsB was found to maintain a very high-specific activity for propionyl-CoA in allylmalonyl-CoA biosynthetic work and S. glaucescens FabH which use isobutyryl-CoA as substrate can initiate methyl side chain biosynthesis in 36-methyl-FK506 in ΔTcsB.
NGLC 2004-2010.National Geological Library of China All Rights Reserved.
Add:29 Xueyuan Rd,Haidian District,Beijing,PRC. Mail Add: 8324 mailbox 100083
For exchange or info please contact us via email.