Skip to main content
SpringerLink
Log in
SpringerLink
Log in

The chemistry and biology of fatty acid, polyketide, and nonribosomal peptide biosynthesis

  • Chapter
  • First Online:
Bioorganic Chemistry Deoxysugars, Polyketides and Related Classes: Synthesis, Biosynthesis, Enzymes

Part of the book series: Topics in Current Chemistry ((4143,volume 188))

Abstract

Polyketide synthases, fatty acid synthases, and non-ribosomal peptide synthetases are a structurally and mechanistically related class of enzymes that catalyze the synthesis of biopolymers in the absence of a nucleic acid or other template. These enzymes utilize the common mechanistic feature of activating monomers for condensation via covalently-bound thioesters of phosphopantetheine prosthetic groups. The information for the sequence and length of the resulting polymer appears to be encoded entirely within the responsible proteins.

Polyketide and fatty acid biosyntheses begin with condensation of the coenzyme A thioester of a short-chain carboxylic acid “starter unit” such as acetate or propionate with the coenzyme A thioester of a dicarboxylic acid “extender unit” such as malonate or methyl malonate. The driving force for the condensation is provided by the decarboxylation of the extender unit. In the case of fatty acid synthesis, the resulting β-carbonyl is completely reduced to a methylene; however, during the synthesis of complex polyketides, the β-carbonyl may be left untouched or variably reduced to alcohol, olefinic, or methylene functionalities depending on the position that the extender unit will occupy in the final product. This cycle is repeated, and the number of elongation cycles is a characteristic of the enzyme catalyst. In polyketide biosynthesis, the full-length polyketide chain cyclizes in a specific manner, and is tailored by the action of additional enzymes in the pathway.

Several architectural paradigms are known for polyketide and fatty acid synthases. While the bacterial enzymes are composed of several monofunctional polypeptides which are used during each cycle of chain elongation, fatty acid and polyketide synthases in higher organisms are multifunctional proteins with an individual set of active sites dedicated to each cycle of condensation and ketoreduction. Peptide synthetases also exhibit a one-to-one correspondence between the enzyme sequence and the structure of the product. Together, these systems represent a unique mechanism for the synthesis of biopolymers in which the template and the catalyst are the same molecule.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. O’Hagan D (1995) Nat Prod Rep 12:1

    Article  CAS  Google Scholar 

  2. Collie N (1893) J Chem Soc 122

    Google Scholar 

  3. Davis NK, Chater KF (1990) Mol Microbiol 4:1679

    Article  CAS  Google Scholar 

  4. Durbin ML, Learn GH, Huttley GA, Clegg MT (1995) Proc Natl Acad Sci, USA 92:3338

    Article  CAS  Google Scholar 

  5. Hopwood DA, Khosla C (1992) Ciba Found Symp 171:88

    CAS  Google Scholar 

  6. Katz L, Donadio S (1993) Annu Rev Microbiol 47: 875

    Article  CAS  Google Scholar 

  7. Hutchinson CR, Fujii I (1995) Annu Rev Microbiol 49:201

    Article  CAS  Google Scholar 

  8. O’Hagan D (1991) The Polyketide Metabolites. Ellis Horwood, Chichester, UK

    Google Scholar 

  9. O’Hagan D (1992) Nat Prod Rep 9:447

    Article  CAS  Google Scholar 

  10. O’Hagan D (1993) Nat Prod Rep 10:593

    Article  CAS  Google Scholar 

  11. Simpson TJ (1995) Chemistry & Industry 11:407

    Google Scholar 

  12. Magnuson K, Jackowski S, Rock CO, Cronan JEJ (1993) Microbiol Rev 57:522

    CAS  Google Scholar 

  13. Fernandez-Moreno MA, Martinez E, Boto L, Hopwood DA, Malpartida F (1992) J Biol Chem 267:19278

    CAS  Google Scholar 

  14. Sherman DH, Malpartida F, Bibb MJ, Kieser HM, Bibb MJ, Hopwood DA (1989) EMBO J 8:2717

    CAS  Google Scholar 

  15. Bibb MJ, Biró S, Motamedi H, Collins JF, Hutchinson CR (1989) EMBO J 8:2727

    CAS  Google Scholar 

  16. Chirala SS, Kuziora MA, Spector DM, Wakil SJ (1987) J Biol Chem 262:4231

    CAS  Google Scholar 

  17. Mohamed AH, Chirala SS, Mody NH, Huang WY, Wakil SJ (1988) J Biol Chem 263:12315

    CAS  Google Scholar 

  18. Holzer KP, Liu W, Hammes GG (1990) Proc Natl Acad Sci, USA 86:4523

    Google Scholar 

  19. Witkowski A, Rangan VS, Randhawa ZI, Amy CM, Smith S (1991) Eur J Biochem 198:571

    Article  CAS  Google Scholar 

  20. Schweizer M, Takabayashi K, Laux T, Beck K-F, Schreglmann R (1989) Nuc Acid Res 17: 567

    Article  CAS  Google Scholar 

  21. Amy C, Witkowski A, Naggert J, Williams B, Randhawa Z, Smith S (1989) Proc Natl Acad Sci, USA 86:3114

    Article  CAS  Google Scholar 

  22. Beck J, Ripka S, Siegner A, Schiltz E, Schweizer E (1990) Eur J Biochem 192:487

    Article  CAS  Google Scholar 

  23. Cortes J, Haydock SF, Roberts GA, Bevitt DJ, Leadlay PF (1990) Nature 348:176

    Article  CAS  Google Scholar 

  24. Donadio S, Staver MJ, J.B. M., Swanson SJ, Katz L (1991) Science 252:675

    Article  CAS  Google Scholar 

  25. MacNeil DJ, Occi JL, Gewain KM, MacNeil T, Gibbons PH, Ruby CL, Danis SJ (1992) Gene 115:119

    Article  CAS  Google Scholar 

  26. Schwecke T, Aparacio JF, Molnar I, König A, Khaw L, Haydock SF, Oliynyk M, Caffrey P, Cortes J, Lester JB, Böhm GA, Staunton J, Leadlay PF (1995) Proc Natl Acad Sci, USA 92:7839

    Article  CAS  Google Scholar 

  27. Schröder G, Schröder J (1992) J Biol Chem 267:20558

    Google Scholar 

  28. Stryer L (1995) Biochemistry. 4th edn, WH Freeman, New York

    Google Scholar 

  29. Wakil SJ, Stoops JK, Joshi VC (1983) Ann Rev Biochem 52:537

    Article  CAS  Google Scholar 

  30. Smith S (1994) FASEB J 8:1248

    CAS  Google Scholar 

  31. Wakil S (1989) Biochemistry 28:4523

    Article  CAS  Google Scholar 

  32. Schorr R, Mittag M, Müller G, Schweizer E (1994) J Plant Phisiol 143:407

    CAS  Google Scholar 

  33. Stoops JK, Kolodziej SJ, Schroeter JP, Bretaudiere JP (1992) Proc Natl Acad Sci, USA 89:6585

    Article  CAS  Google Scholar 

  34. Stoops JK, Wakil SJ, Uberbacher EC, Bunick GJ (1987) J Biol Chem 262:10246

    CAS  Google Scholar 

  35. Holak TA, Nilges M, Prestegard JH, Grononborn AM, Clore GM (1988) Eur J Biochem 179:9

    Article  Google Scholar 

  36. Serre L, Verbree EC, Dauter Z, Stuitje AR, Derewenda ZS (1995) J Biol Chem 270:12961

    Article  CAS  Google Scholar 

  37. Dessen A, Quémard A, Blanchard JS, Jacobs WRJ, Sacchettini JC (1995) Science 267:1638

    Article  CAS  Google Scholar 

  38. Olsen JG, Kadziola A, Siggaard-Andersen M, Chuck J, Larsen S, von Wettstein-Knowles P (1995) Prot Pep Lett 1:246

    CAS  Google Scholar 

  39. Guchhait RB, Polakis E, Dimroth P, Stoll E, Moss J, Lane MD (1974) J Biol Chem 249:6633

    CAS  Google Scholar 

  40. Polakis SE, Guchhait RB, Zwergel EE, Lane MD, Cooper TG (1974) J Biol Chem 244:6657

    Google Scholar 

  41. Al-Feel W, Chirala SS, Wakil SJ (1992) Proc Natl Acad Sci, USA 89:4534

    Article  CAS  Google Scholar 

  42. Takai T, Yokoyama C, Wada K, Tanabe T (1988) J Biol Chem 263:2651

    CAS  Google Scholar 

  43. Vagelos PR (1973) Acyl group transfer (acyl carrier protein). In: The enzymes. Academic, New York, p 155

    Google Scholar 

  44. Rawlings M, Cronan JEJ (1992) J Biol Chem 267:5751

    CAS  Google Scholar 

  45. Jones AL, Kille P, Dancer JE, Harwood JL (1993) Biochem Soc Trans 21:202S

    CAS  Google Scholar 

  46. Lambalot RH, Walsh CT (1995) J Biol Chem 270:24658

    Article  CAS  Google Scholar 

  47. Jackowski S, Murphy CM, Cronan JEJ, Rock CO (1989) J Biol Chem 264:7624

    CAS  Google Scholar 

  48. Jackowski S, Rock CO (1987) J Biol Chem 262:7927

    CAS  Google Scholar 

  49. Stroud RM (1974) Sci Amer 231:24

    Article  Google Scholar 

  50. Perona JJ, Craik CS (1995) Prot Sci 4:337

    Article  CAS  Google Scholar 

  51. Siggaard-Andersen M (1993) Prot Seq Data Anal 5:325

    CAS  Google Scholar 

  52. Siggaard-Andersen M, Wissenbach M, Chuck J, Svendsen I, Olsen JG, von Wettstein-Knowles P (1994) Proc Natl Acad Sci, USA 91:11027

    Article  CAS  Google Scholar 

  53. Magnuson K, Carey MR, Cronan JE (1995) J Bact 177:3593

    CAS  Google Scholar 

  54. Dewar MJS, Dieter KM (1988) Biochem 27:3302

    Article  CAS  Google Scholar 

  55. Heath RJ, Rock CO (1995) J Biol Chem 270:26538

    Article  CAS  Google Scholar 

  56. Rossman MG, Liljas A, Granden C, Banaszak L (1975) In: The enzymes. Academic, New York, p 61

    Google Scholar 

  57. Stoops JK, Wakil SJ (1978) Biochem Biophys Res Comm 84:225

    Article  CAS  Google Scholar 

  58. Schweizer E, Werkmeister K, Jain J (1978) Mol Cell Biochem 21:95

    Article  CAS  Google Scholar 

  59. Kresze GB, Oesterhelt D, Lynen F, Castorph H, Schweizer E (1976) Biochem Biophys Res Comm 69:893

    Article  CAS  Google Scholar 

  60. Stoops JK, Awad ES, Arslain MJ, Gunsberg S, Wakil SJ, Oliver RM (1978) J Biol Chem 253:4464

    CAS  Google Scholar 

  61. Stoops JK, Wakil SJ (1980) Proc Natl Acad Sci, USA 77:4544

    Article  CAS  Google Scholar 

  62. Stoops JK, Wakil SJ (1981) J Biol Chem 256:8364

    CAS  Google Scholar 

  63. Schweizer E, Piccinini F, Duba C, Gunter S, Ritter E, Lynen F (1970) Eur J Biochem 15:483

    Article  CAS  Google Scholar 

  64. Oesterhelt D, Bauer H, Lynen F (1969) Proc Natl Acad Sci, USA 63:1377

    Article  CAS  Google Scholar 

  65. Oesterhelt D, Bauer H, Kresze GB, Steber L, Lynen F (1977) Eur J Biochem 79:173

    Article  CAS  Google Scholar 

  66. Schweizer R (1984) In: Fatty acid metabolism and its regulation. Elsevier, Amsterdam, p 59

    Google Scholar 

  67. Singh N, Wakil SJ, Stoops JK (1985) Biochem 24:6598

    Article  CAS  Google Scholar 

  68. Singh N, Wakil SJ, Stoops JK (1985) Biochem Biophys Res Comm 131:786

    Article  CAS  Google Scholar 

  69. Schuster H, Rautenstrauss B, Mittag M, Stratmann D, Schweizer E (1995) Eur J Biochem 228:417

    Article  CAS  Google Scholar 

  70. Ziegenhorn J, Niedermeier R, Nüssler C, Lynen F (1972) Eur J Biochem 30:285

    Article  CAS  Google Scholar 

  71. Engeser H, Hübner K, Straub J, Lynen F (1979) Eur J Biochem 101:407

    Article  CAS  Google Scholar 

  72. Engeser H, Hübner K, Straub J, Lynen F (1979) Eur J Biochem 101

    Google Scholar 

  73. Stoops JK, Singh N, Wakil SJ (1990) J Biol Chem 265:16971

    CAS  Google Scholar 

  74. Katiyar SS, Briedis AV, Porter JW (1974) Arch Biochem Biophys 162:412

    Article  CAS  Google Scholar 

  75. Kresze GB, Steber L, Oesterhelt D, Lynen F (1977) Eur J Biochem 79:191

    Article  CAS  Google Scholar 

  76. Stoops JK, Ross P, Arslanian MJ, Aune KC, Wakil SJ, Oliver RM (1979) J Biol Chem 254:3194

    Google Scholar 

  77. Stoops JK, Wakil SJ (1981) J Biol Chem 256:5128

    CAS  Google Scholar 

  78. Kitamoto T, Nishigai M, Sasaki T, Ikai A (1988) J Mol Biol 203:1823

    Article  Google Scholar 

  79. Stoops JK, Wakil SJ (1982) J Biol Chem 257:3230

    CAS  Google Scholar 

  80. Stoops JK, Henry SJ, Wakil SJ (1983) J Biol Chem 258:12482

    CAS  Google Scholar 

  81. Wang YS, Tian WX, Hsu RY (1984) J Biol Chem 259:13644

    CAS  Google Scholar 

  82. Singh N, Wakil SJ, Stoops JK (1984) J Biol Chem 259:3605

    CAS  Google Scholar 

  83. Joshi AK, Smith S (1993) J Biol Chem 268:22508

    CAS  Google Scholar 

  84. Foster RJ, Poulose AJ, Bonsall RF, Kolattukudy PE (1985) J Biol Chem 260:2826

    CAS  Google Scholar 

  85. Yuan ZY, Hammes GG (1986) J Biol Chem 261:13643

    CAS  Google Scholar 

  86. Chang SI and Hammes GG (1989) Biochem 28:3781

    Article  CAS  Google Scholar 

  87. Witkowski A, Naggert J, Wessa B, Smith S (1991) J Biol Chem 267:18488

    Google Scholar 

  88. Smith S (1981) Meth Enz 71C: 188

    Google Scholar 

  89. Knudsen J, Grunnet I, Dils R (1981) Biochem J 186:287

    Google Scholar 

  90. Krätzschmar J, Krause M, Marahiel MA (1989) J Bacteriol 171:5422

    Google Scholar 

  91. Raibaud A, Zalacain M, Holt TG, Tizard R, Thompson CJ (1991) J Bacteriol 173:4454

    CAS  Google Scholar 

  92. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) Science 262:1546

    Article  CAS  Google Scholar 

  93. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1993) J Am Chem Soc 115:11671

    Article  CAS  Google Scholar 

  94. Bartel PL, Zhu CB, Lampel JS, Dosch DC, Conners NC, Strohl WR, Beale JM, Floss HG (1990) J Bact 172:4816

    CAS  Google Scholar 

  95. Fu H, Ebert-Khosla S, Hopwood DA, Khosla C (1994) J Am Chem Soc 116:4166

    Article  CAS  Google Scholar 

  96. McDaniel R, Ebert-Khosla S, Fu H, Hopwood DA, Khosla C (1994) Proc Natl Acad Sci, USA 91:11542

    Article  CAS  Google Scholar 

  97. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1994) J Am Chem Soc 116:10855

    Article  CAS  Google Scholar 

  98. B, Summers RG, Wendtpienkowski E, Hutchinson CR (1995) J Am Chem Soc 117:6811

    Article  Google Scholar 

  99. McDaniel R, Hutchinson CR, Khosla C (1995) J Am Chem Soc 117:6805

    Article  CAS  Google Scholar 

  100. Malpartida F, Hopwood DA (1984) Nature 309:462

    Article  CAS  Google Scholar 

  101. Hallam SE, Malpartida F, Hopwood DA (1988) Gene 74:305

    Article  CAS  Google Scholar 

  102. Yu TW (1995) PhD thesis, University of East Anglia

    Google Scholar 

  103. H, Hopwood DA, Khosla C (1994) Chem & Biol 1:205

    Article  Google Scholar 

  104. McDaniel R, Ebert-Khosla S, Hopwood DA, Khosla C (1995) Nature 375:549

    Article  CAS  Google Scholar 

  105. Summers RG, Wendt-Pienkowski E, Motamedi H, Hutchinson CR (1992) J Bacteriol 174:1810

    CAS  Google Scholar 

  106. Shen B, Hutchinson CR (1993) Science 262:1535

    Article  CAS  Google Scholar 

  107. Carreras CW, Pieper R, Khosla C (1996) J Am Chem Soc 118:185

    Article  Google Scholar 

  108. Shen B, Nakayama H, Hutchinson CR (1993) J Nat Prod 56:1288

    Article  CAS  Google Scholar 

  109. Shen B, Hutchinson CR (1993) Biochem 32

    Google Scholar 

  110. Shen B, Hutchinson CR (1993) Biochem 32:6656

    Article  CAS  Google Scholar 

  111. Crosby J, Sherman DH, Bibb MJ, Revill WP, Hopwood DA, Simpson TJ (1995) Biochim Biophys Acta 1251:32

    Google Scholar 

  112. Shen B, Summers RG, Gramajo H, Bibb MJ, Hutchinson CR (1992) J Bact 174:3818

    CAS  Google Scholar 

  113. Lynen F, Tada M (1961) Angew Chem 73:513

    Article  CAS  Google Scholar 

  114. Gaucher GM, Shepherd MG (1968) Biochem Biophys Res Comm 32:664

    Article  CAS  Google Scholar 

  115. Dimroth P, Walter H, Lynen F (1971) Eur J Biochem 13:98

    Article  Google Scholar 

  116. Martin JF, Demain AL (1978) In: The filamentous fungi. Edward Arnold, London, p 426

    Google Scholar 

  117. Pflügl G, Kallen J, Schirmer T, Jansonius JN, Zurini MGM, Walkinshaw MD (1993) Nature 49: 91

    Article  Google Scholar 

  118. Kobel H, Loosli HR, Voges R (1983) Experientia (Basel) 39:873

    CAS  Google Scholar 

  119. Offenzeller M, Su Z, Santer G, Moser H, Traber R, Memmert K, Schneider-Scherzer E (1993) J Biol Chem 268:26127

    CAS  Google Scholar 

  120. Spencer JB, Jordan PM (1992) Biochem J 288:839

    CAS  Google Scholar 

  121. Dimroth P, Walter H, Lynen F (1970) Eur J Biochem 13:98

    Article  CAS  Google Scholar 

  122. Scott AI, Beadling LC, Georgopapadakou NH, Subbarayan CR (1974) Bioorg Chem 3:238

    Article  CAS  Google Scholar 

  123. Vogel G, Lynen F (1976) Meth Enz 43:520

    Google Scholar 

  124. Dimroth P, Greull G, Seyfferet R, Lynen F (1972) Hoppe Syler’s Z Physiol Chem 353:126

    CAS  Google Scholar 

  125. Dimroth P, Ringelmann E, Lynen F (1976) Eur J Biochem 68:591

    Article  CAS  Google Scholar 

  126. Bhogal P, Shoolingin-Jordan P. Incorporation of novel substrates into 6-methylsalicylic acid and triacetic acid lactone analogues by 6-methyl salicylic acid synthase. In: Polyketides: chemistry, biochemistry, molecular genetics. 1996. Royal Society of Chemistry, Bristol, UK, p 19

    Google Scholar 

  127. Jordan PM, Spencer JB (1990) J Chem Soc, Chem Comm 238

    Google Scholar 

  128. Spencer JB, Jordan PM (1992) Biochemistry 31:9107

    Article  CAS  Google Scholar 

  129. Woo ER, Fujii I, Ebizuka Y, Sankawa U, Floss H (1989) J Am Chem Soc 111:5498

    Article  CAS  Google Scholar 

  130. Jordan PM, Spencer JB (1993) Biochem Soc Trans 21:222

    CAS  Google Scholar 

  131. Bedford DJ, Schweizer E, Hopwood DA, Khosla C (1995) J Bact 117:4544

    Google Scholar 

  132. Schröder J, Schröder G (1990) Z Naturforsch 45c: 1

    Google Scholar 

  133. Hopwood DA, Sherman DH (1990) Annu Rev Genet 24:37

    Article  CAS  Google Scholar 

  134. Lanz T, Tropf S, Marner FJ, Schröder J, Schröder G (1991) J Biol Chem 266:9971

    CAS  Google Scholar 

  135. Schöppner A, Kindl H (1984) J Biol Chem 259:6806

    Google Scholar 

  136. Tropf S, Kärcher B, Schröder G, Schröder J (1995) J Biol Chem 270:7922

    Article  CAS  Google Scholar 

  137. Schüz R, Heller W, Hahlbrock (1983) J Biol Chem 258:6730

    Google Scholar 

  138. Fliegmann J, Schröder G, Schanz S, Britsch L, Schröder J (1992) Plant Mol Biol 18:489

    Article  CAS  Google Scholar 

  139. Woodward RB (1957) Angew Chem 69:50

    Article  CAS  Google Scholar 

  140. Gerzon K, Flynn EH, Sigal MV, Wiley PF, Monahan R, Quarck UC (1956) J Am Chem Soc 78:6398

    Google Scholar 

  141. Griesebach H, Achenbach H, Hofheinz W (1960) Z Naturforschg 15b:560

    Google Scholar 

  142. Kaneda T, Butte JC, Taubman SB, Corcoran JW (1962) J Biol Chem 237:322

    CAS  Google Scholar 

  143. Cane DE, Hasler H, Taylor PB, Liang TC (1983) Tetrahedron 39:3449

    Article  CAS  Google Scholar 

  144. Cane DE, Celmer WD, Westley JW (1983) J Am Chem Soc 105:3594

    Article  CAS  Google Scholar 

  145. Cane DE, Liang TC, Taylor PB, Chang C, Yang CC (1986) J Am Chem Soc 108:4957

    Article  CAS  Google Scholar 

  146. Cane DE, Yang CC (1987) J Am Chem Soc 109:1255

    Article  CAS  Google Scholar 

  147. Cane DE, Ott WR (1988) J Am Chem Soc 110:4840

    Article  CAS  Google Scholar 

  148. Caffrey P, Bevitt DJ, Staunton J, Leadlay PF (1992) FEBS Lett 304:225

    Article  CAS  Google Scholar 

  149. Roberts GA, Staunton J, Leadlay PF (1993) Eur J Biochem 214:305

    Article  CAS  Google Scholar 

  150. Marsden AFA, Caffrey P, Aparicio JF, Loughran MS, Staunton J, Leadley PF (1994) Science 263:378

    Article  CAS  Google Scholar 

  151. Aparicio J, Caffery P, A.F.A. M, Staunton J, Leadley PF (1994) J Biol Chem 269:8524

    CAS  Google Scholar 

  152. Staunton J, Caffrey P, Apaicio JF, Roberts GA, Bethell SS, Leadlay PF (1996) Nature Struct Biol 3:188

    Article  CAS  Google Scholar 

  153. Donadio S, McAlpine JB, Sheldon PJ, Jackson M, Katz L (1993) Proc Natl Acad Sci, USA 90:7119

    Article  CAS  Google Scholar 

  154. Kao CM, Katz L, Khosla C (1994) Science 265:509

    Article  CAS  Google Scholar 

  155. Kao CM, Luo G, Katz L, Cane DE, Khosla C (1994) J Am Chem Soc 116:11612

    Article  CAS  Google Scholar 

  156. Cortes J, Wiesmann KEH, Roberts GA, Brown MJB, Staunton J, Leadlay PF (1995) Science 268:1487

    Article  CAS  Google Scholar 

  157. Kao CM, Luo G, Katz L, Cane DE, Khosla C (1995) J Am Chem Soc 117:9105

    Article  Google Scholar 

  158. Kao CM, Luo G, Katz L, Cane DE, Khosla C (1996) J Am Chem Soc, 118:9184

    Article  CAS  Google Scholar 

  159. Pieper R, Luo G, Cane DE, Khosla C (1995) Nature 378:263

    Article  CAS  Google Scholar 

  160. Wiesmann KEH, Cortés J, Brown MJB, Cutter AL, Staunton J, Leadlay PF (1995) Chem & Biol 2:583

    Article  CAS  Google Scholar 

  161. Pieper R, Luo G, Cane DE, Khosla C (1995) J Am Chem Soc 117:11373

    Article  CAS  Google Scholar 

  162. Luo G, Pieper R, Rose A, Khosla C, Cane DE (1996) Bioorg Med Chem 4:995–999

    Article  CAS  Google Scholar 

  163. Pieper R, Ebert-Khosla S, Cane D, Khosla C (1996) Biochem 35:2054

    Article  CAS  Google Scholar 

  164. Swan DG, Rodriguez AM, Vilches C, Mendez C, Salas JA (1994) Mol Gen Genet 242:358

    Article  CAS  Google Scholar 

  165. Schupp T, Toupet C, Cluzel B, Neff S, Hill S, Beck JJ, Ligon JM (1995) J Bact 177:3673

    CAS  Google Scholar 

  166. Lipmann F (1980) Adv Microbiol Physiol 21:227

    Article  CAS  Google Scholar 

  167. Kleinkauf H, von Doehren H (1990) Eur J Biochem 192:1

    Article  CAS  Google Scholar 

  168. Zuber P, Nakano MM, Marahiel MA (1993) Am Soc Microbiol, Washington, DC, p 897

    Google Scholar 

  169. Kleinkauf H, v. Döhren H (1996) Eur J Biochem 236:335

    Article  CAS  Google Scholar 

  170. Lipmann F (1954) In: The mechanisms of enzyme action. Johns Hopkins University, Baltimore, p 599

    Google Scholar 

  171. Laland SG, Froyshov O, Gilhuus-Moe CC, Zimmer TL (1972) Nature 239:43

    Article  CAS  Google Scholar 

  172. Laland SG, Zimmer TL (1973) Essays Biochem 9:31

    CAS  Google Scholar 

  173. Lipmann F (1973) Acc Chem Res 6:361

    Article  CAS  Google Scholar 

  174. Kleinkauf H, Roskoski R, Lipmann F (1971) Proc Natl Acad Sci 68:2069

    Article  CAS  Google Scholar 

  175. Gilhuus-Moe CC, Kristensen T, Bredesen JE, Zimmer TL, Laland SG (1970) FEBS Lett 7:287

    Article  CAS  Google Scholar 

  176. Diez B, Gutierrez S, Barredo JL, van Solingen P, van der Voort LHM, Martin JF (1990) J Biol Chem 265:16358

    CAS  Google Scholar 

  177. Smith DJ, Earl AJ, Turner G (1990) EMBO J 9:2743

    CAS  Google Scholar 

  178. Weckermann R, Fuerbass R, Marahiel MA (1988) Nucl Acids Res 16:11841

    Article  CAS  Google Scholar 

  179. Stachelhaus T, Marahiel MA (1995) FEMS Microbiol Lett 125:3

    Article  CAS  Google Scholar 

  180. Stachelhaus T, Marahiel MA (1995) J Biol Chem 11:6163

    Google Scholar 

  181. Haese A, Pieper R, von Ostrowski T, Zocher R (1994) J Mol Biol 243:116

    Article  CAS  Google Scholar 

  182. Weber G, Schoergendorfer K, Schneider-Scherzer E, Leitner E (1994) Current Genetics 26:120

    Article  CAS  Google Scholar 

  183. Gocht M, Marahiel MA (1994) J Bacteriol 176:2654

    CAS  Google Scholar 

  184. Heaton MP, Neuhaus FC (1994) J Bact 176:681

    CAS  Google Scholar 

  185. Haese A, Schubert M, Herrmann M, Zocher R (1993) Mol Microbiol 7:905

    Article  CAS  Google Scholar 

  186. Turgay K, Krause M, Marahiel MA (1992) Molec Microbiol 6:529

    Article  CAS  Google Scholar 

  187. Hamoen LW, Eshuis H, Jongbloed J, Venema G, van Sinderen D (1995) Mol Microbiol 15:55

    Article  CAS  Google Scholar 

  188. Saito M, Hori K, Kurotsu T, Kaneda M, Saito Y (1995) J Biochem (Tokyo) 117:276

    CAS  Google Scholar 

  189. Tokita K, Hori K, Kurotsu T, Kanda M, Saito Y (1993) J Biochem (Tokyo) 114:522

    CAS  Google Scholar 

  190. Pavela-Vrancic M, Pfeifer E, van Liempt H, Schäfer H-J, von Döhren H, Kleinkauf H (1994) Biochem 33:6276

    Article  CAS  Google Scholar 

  191. Schlumbohm W, Stein TU, C., Vater J, Krause M, Marahiel MA (1991) J Biol Chem 266: 23135

    CAS  Google Scholar 

  192. Stein T, Vater J, Kruft V, Wittmann-Liebold B, Franke P, Panico M, McDowell R, Morris HR (1994) FEBS Lett 340:39

    Article  CAS  Google Scholar 

  193. Hoffmann K, Schneider-Scherzer E, Kleinkauf H, Zocher R (1994) J Biol Chem 269:12710

    CAS  Google Scholar 

  194. Yamada M and Kurahashi K (1969) J Biochem 66:529

    CAS  Google Scholar 

  195. Kanda M, Hori K, Kurotsu T, Miura S, Yamada Y, Saito Y (1981) J Biochem (Tokyo) 90:765

    CAS  Google Scholar 

  196. Kanda M, Hori K, Kurotsu T, Miura S, Saito Y (1989) J Biochem (Tokyo) 105:653

    CAS  Google Scholar 

  197. Hori K, Saito F, Tokita K, Kurotsu T, Kanda M, Saito Y (1994) J Biochem (Tokyo) 116:1202

    CAS  Google Scholar 

  198. Stindl A, Keller U (1994) Biochemistry 33:9358

    Article  CAS  Google Scholar 

  199. Billich A, Zocher R (1987) Biochemistry 26:8417

    Article  CAS  Google Scholar 

  200. Pieper R, Haese A, Schroeder W, Zocher R (1995) Eur J Biochem 230:119

    Article  CAS  Google Scholar 

  201. Cosmina P, Rodriguez F, deFerra F, Perego M, Venema G, van Sinderen D (1993) Molec Microbiol 8:821

    Article  CAS  Google Scholar 

  202. Zocher R, Keller U, Kleinkauf H (1982) Biochem 21:43

    Article  CAS  Google Scholar 

  203. Lawen A, Traber A, Geyl D, Zocher R, Kleinkauf H (1989) J Antibiot 42:1283

    CAS  Google Scholar 

  204. Plattner PA, Nager U, Boller A (1948) Helv Chim Acta 31:594

    Article  CAS  Google Scholar 

  205. Traber R, Hofman H, Kobel H (1989) J Antibiot 25:1

    Google Scholar 

  206. Stachelhaus T, Schneider A, Marahiel MA (1995) Science 269:69

    Article  CAS  Google Scholar 

  207. Fu H, Alvarez MA, Khosla C, Bailey JE (1996) Biochemistry 35:6527

    Article  CAS  Google Scholar 

  208. Donadio S, Staver MJ, McAlpine JB, Swanson SJ, Katz L (1992) Gene 115:97

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemical Engineering and Chemistry, Stanford University, Mail Code #5025, 94305-5025, Stanford, CA, USA

    Christopher W. Carreras, Rembert Pieper & Chaitan Khosla

Authors
  1. Christopher W. Carreras
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rembert Pieper
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chaitan Khosla
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chaitan Khosla .

Editor information

Jürgen Rohr

Rights and permissions

Reprints and permissions

Copyright information

© 1997 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Carreras, C.W., Pieper, R., Khosla, C. (1997). The chemistry and biology of fatty acid, polyketide, and nonribosomal peptide biosynthesis. In: Rohr, J. (eds) Bioorganic Chemistry Deoxysugars, Polyketides and Related Classes: Synthesis, Biosynthesis, Enzymes. Topics in Current Chemistry, vol 188. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119235

Download citation

  • DOI: https://doi.org/10.1007/BFb0119235

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-62488-2

  • Online ISBN: 978-3-540-68024-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation