Genes and Enzymes Involved in Caffeic Acid Biosynthesis in the Actinomycete Saccharothrix Espanaensis

Overview

Journal J Bacteriol

Publisher American Society for Microbiology

Specialty Microbiology

Date 2006 Mar 21

PMID 16547054

Citations 52

Authors

Martin Berner

Daniel Krug

Corina Bihlmaier

Andreas Vente

Rolf Muller

Andreas Bechthold

Affiliations

Soon will be listed here.

Abstract

The saccharomicins A and B, produced by the actinomycete Saccharothrix espanaensis, are oligosaccharide antibiotics. They consist of 17 monosaccharide units and the unique aglycon N-(m,p-dihydroxycinnamoyl)taurine. To investigate candidate genes responsible for the formation of trans-m,p-dihydroxycinnamic acid (caffeic acid) as part of the saccharomicin aglycon, gene expression experiments were carried out in Streptomyces fradiae XKS. It is shown that the biosynthetic pathway for trans-caffeic acid proceeds from L-tyrosine via trans-p-coumaric acid directly to trans-caffeic acid, since heterologous expression of sam8, encoding a tyrosine ammonia-lyase, led to the production of trans-p-hydroxycinnamic acid (coumaric acid), and coexpression of sam8 and sam5, the latter encoding a 4-coumarate 3-hydroxylase, led to the production of trans-m,p-dihydroxycinnamic acid. This is not in accordance with the general phenylpropanoid pathway in plants, where trans-p-coumaric acid is first activated before the 3-hydroxylation of its ring takes place.

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References

Von Mulert U, Luzhetskyy A, Hofmann C, Mayer A, Bechthold A . Expression of the landomycin biosynthetic gene cluster in a PKS mutant of Streptomyces fradiae is dependent on the coexpression of a putative transcriptional activator gene. FEMS Microbiol Lett. 2004; 230(1):91-7. DOI: 10.1016/S0378-1097(03)00861-9. View

Nair R, Xia Q, Kartha C, Kurylo E, Hirji R, Datla R . Arabidopsis CYP98A3 mediating aromatic 3-hydroxylation. Developmental regulation of the gene, and expression in yeast. Plant Physiol. 2002; 130(1):210-20. PMC: 166554. DOI: 10.1104/pp.008649. View

Doumith M, WEINGARTEN P, Wehmeier U, Benhamou B, Capdevila C, Michel J . Analysis of genes involved in 6-deoxyhexose biosynthesis and transfer in Saccharopolyspora erythraea. Mol Gen Genet. 2000; 264(4):477-85. DOI: 10.1007/s004380000329. View

Rother D, Poppe L, Viergutz S, Langer B, Retey J . Characterization of the active site of histidine ammonia-lyase from Pseudomonas putida. Eur J Biochem. 2001; 268(23):6011-9. DOI: 10.1046/j.0014-2956.2001.02298.x. View

Christenson S, Liu W, Toney M, Shen B . A novel 4-methylideneimidazole-5-one-containing tyrosine aminomutase in enediyne antitumor antibiotic C-1027 biosynthesis. J Am Chem Soc. 2003; 125(20):6062-3. DOI: 10.1021/ja034609m. View

Humphreys J, Chapple C . Rewriting the lignin roadmap. Curr Opin Plant Biol. 2002; 5(3):224-9. DOI: 10.1016/s1369-5266(02)00257-1. View

Calabrese J, Jordan D, Boodhoo A, Sariaslani S, Vannelli T . Crystal structure of phenylalanine ammonia lyase: multiple helix dipoles implicated in catalysis. Biochemistry. 2004; 43(36):11403-16. DOI: 10.1021/bi049053+. View

Buck R, Krummen K . High-performance liquid chromatographic determination of enantiomeric amino acids and amino alcohols after derivatization with o-phthaldialdehyde and various chiral mercaptans. Application to peptide hydrolysates. J Chromatogr. 1987; 387:255-65. DOI: 10.1016/s0021-9673(01)94529-7. View

Franke R, Hemm M, Denault J, Ruegger M, Humphreys J, Chapple C . Changes in secondary metabolism and deposition of an unusual lignin in the ref8 mutant of Arabidopsis. Plant J. 2002; 30(1):47-59. DOI: 10.1046/j.1365-313x.2002.01267.x. View

10.

Schwede T, Retey J, Schulz G . Crystal structure of histidine ammonia-lyase revealing a novel polypeptide modification as the catalytic electrophile. Biochemistry. 1999; 38(17):5355-61. DOI: 10.1021/bi982929q. View

11.

Christenson S, Wu W, Spies M, Shen B, Toney M . Kinetic analysis of the 4-methylideneimidazole-5-one-containing tyrosine aminomutase in enediyne antitumor antibiotic C-1027 biosynthesis. Biochemistry. 2003; 42(43):12708-18. DOI: 10.1021/bi035223r. View

12.

Kyndt J, Meyer T, Cusanovich M, Van Beeumen J . Characterization of a bacterial tyrosine ammonia lyase, a biosynthetic enzyme for the photoactive yellow protein. FEBS Lett. 2002; 512(1-3):240-4. DOI: 10.1016/s0014-5793(02)02272-x. View

13.

Franke R, Humphreys J, Hemm M, Denault J, Ruegger M, Cusumano J . The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism. Plant J. 2002; 30(1):33-45. DOI: 10.1046/j.1365-313x.2002.01266.x. View

14.

Heller W, Kuhnl T . Elicitor induction of a microsomal 5-O-(4-coumaroyl)shikimate 3'-hydroxylase in parsley cell suspension cultures. Arch Biochem Biophys. 1985; 241(2):453-60. DOI: 10.1016/0003-9861(85)90570-3. View

15.

Appert C, Logemann E, Hahlbrock K, Schmid J, Amrhein N . Structural and catalytic properties of the four phenylalanine ammonia-lyase isoenzymes from parsley (Petroselinum crispum Nym.). Eur J Biochem. 1994; 225(1):491-9. DOI: 10.1111/j.1432-1033.1994.00491.x. View

16.

Labeda D, Kroppenstedt R . Phylogenetic analysis of Saccharothrix and related taxa: proposal for Actinosynnemataceae fam. nov. Int J Syst Evol Microbiol. 2000; 50 Pt 1:331-336. DOI: 10.1099/00207713-50-1-331. View

17.

Williams J, Thomas M, Clarke D . The gene stlA encodes a phenylalanine ammonia-lyase that is involved in the production of a stilbene antibiotic in Photorhabdus luminescens TT01. Microbiology (Reading). 2005; 151(Pt 8):2543-2550. DOI: 10.1099/mic.0.28136-0. View

18.

Xiang L, Moore B . Biochemical characterization of a prokaryotic phenylalanine ammonia lyase. J Bacteriol. 2005; 187(12):4286-9. PMC: 1151709. DOI: 10.1128/JB.187.12.4286-4289.2005. View

19.

Kuhnl T, Koch U, Heller W, Wellmann E . Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-D-quinate/shikimate 3'-hydroxylase from carrot (Daucus carota L.) cell suspension cultures. Arch Biochem Biophys. 1987; 258(1):226-32. DOI: 10.1016/0003-9861(87)90339-0. View

20.

Stafford H, Dresler S . 4-Hydroxycinnamic Acid Hydroxylase and Polyphenolase Activities in Sorghum vulgare. Plant Physiol. 1972; 49(4):590-5. PMC: 366011. DOI: 10.1104/pp.49.4.590. View