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Literature DB >> 19388008

GilR, an unusual lactone-forming enzyme involved in gilvocarcin biosynthesis.

Madan Kumar Kharel¹, Pallab Pahari, Hui Lian, Jürgen Rohr.

Abstract

Last at last: The terminal step of the gilvocarcin V (GV) biosynthetic pathway is an unusual lactone formation. Here we show that the enzyme, GilR, dehydrogenates the hemiacetal moiety of pregilvocarcin V to the lactone found in GV by using covalently bound FAD.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2009 PMID： 19388008 PMCID： PMC2879341 DOI： 10.1002/cbic.200900130

Source DB: PubMed Journal: Chembiochem ISSN： 1439-4227 Impact factor: 3.164

21 in total

1. Crystal structure of the macrocycle-forming thioesterase domain of the erythromycin polyketide synthase: versatility from a unique substrate channel.

Authors: S C Tsai; L J Miercke; J Krucinski; R Gokhale; J C Chen; P G Foster; D E Cane; C Khosla; R M Stroud
Journal: Proc Natl Acad Sci U S A Date: 2001-12-18 Impact factor: 11.205

2. Urdamycin L: a novel metabolic shunt product that provides evidence for the role of the urdM gene in the urdamycin A biosynthetic pathway of Streptomyces fradiae TU 2717.

Authors: Uwe Rix; Lily L Remsing; Dirk Hoffmeister; Andreas Bechthold; Jürgen Rohr
Journal: Chembiochem Date: 2003-01-03 Impact factor: 3.164

3. Cloning, sequencing, and functional analysis of the biosynthetic gene cluster of macrolactam antibiotic vicenistatin in Streptomyces halstedii.

Authors: Yasushi Ogasawara; Kinya Katayama; Atsushi Minami; Miyuki Otsuka; Tadashi Eguchi; Katsumi Kakinuma
Journal: Chem Biol Date: 2004-01

4. Genetic architecture of the polyketide synthases for methymycin and pikromycin series macrolides.

Authors: Y Xue; D Wilson; D H Sherman
Journal: Gene Date: 2000-03-07 Impact factor: 3.688

5. Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: evidence for a specific receptor site and a relation to antitumor activity.

Authors: C Jaxel; K W Kohn; M C Wani; M E Wall; Y Pommier
Journal: Cancer Res Date: 1989-03-15 Impact factor: 12.701

6. Histone H3 and heat shock protein GRP78 are selectively cross-linked to DNA by photoactivated gilvocarcin V in human fibroblasts.

Authors: A Matsumoto; P C Hanawalt
Journal: Cancer Res Date: 2000-07-15 Impact factor: 12.701

7. Gilvocarcins, new antitumor antibiotics. 5. Biosynthesis of gilvocarcins: incorporation of 13C-labeled compounds into gilvocarcin aglycones.

Authors: K Takahashi; F Tomita
Journal: J Antibiot (Tokyo) Date: 1983-11 Impact factor: 2.649

8. Oxidative rearrangement processes in the biosynthesis of gilvocarcin V.

Authors: Tao Liu; Carsten Fischer; Claus Beninga; Jürgen Rohr
Journal: J Am Chem Soc Date: 2004-10-06 Impact factor: 15.419

9. Biosynthesis of chrysomycins A and B. Origin of the chromophore.

Authors: G T Carter; A A Fantini; J C James; D B Borders; R J White
Journal: J Antibiot (Tokyo) Date: 1985-02 Impact factor: 2.649

10. The complete gene cluster of the antitumor agent gilvocarcin V and its implication for the biosynthesis of the gilvocarcins.

Authors: Carsten Fischer; Fredilyn Lipata; Jürgen Rohr
Journal: J Am Chem Soc Date: 2003-07-02 Impact factor: 15.419

12 in total

1. Draft genome of Omphalotus olearius provides a predictive framework for sesquiterpenoid natural product biosynthesis in Basidiomycota.

Authors: Grayson T Wawrzyn; Maureen B Quin; Swati Choudhary; Fernando López-Gallego; Claudia Schmidt-Dannert
Journal: Chem Biol Date: 2012-06-22

2. Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties.

Authors: Micah D Shepherd; Tao Liu; Carmen Méndez; Jose A Salas; Jürgen Rohr
Journal: Appl Environ Microbiol Date: 2010-11-12 Impact factor: 4.792

3. Roles of the synergistic reductive O-methyltransferase GilM and of O-methyltransferase GilMT in the gilvocarcin biosynthetic pathway.

Authors: Nidhi Tibrewal; Theresa E Downey; Steven G Van Lanen; Ehesan Ul Sharif; George A O'Doherty; Jürgen Rohr
Journal: J Am Chem Soc Date: 2012-07-19 Impact factor: 15.419

GilR, an unusual lactone-forming enzyme involved in gilvocarcin biosynthesis.

1. Crystal structure of the macrocycle-forming thioesterase domain of the erythromycin polyketide synthase: versatility from a unique substrate channel.

2. Urdamycin L: a novel metabolic shunt product that provides evidence for the role of the urdM gene in the urdamycin A biosynthetic pathway of Streptomyces fradiae TU 2717.

3. Cloning, sequencing, and functional analysis of the biosynthetic gene cluster of macrolactam antibiotic vicenistatin in Streptomyces halstedii.

4. Genetic architecture of the polyketide synthases for methymycin and pikromycin series macrolides.

5. Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: evidence for a specific receptor site and a relation to antitumor activity.

6. Histone H3 and heat shock protein GRP78 are selectively cross-linked to DNA by photoactivated gilvocarcin V in human fibroblasts.

7. Gilvocarcins, new antitumor antibiotics. 5. Biosynthesis of gilvocarcins: incorporation of 13C-labeled compounds into gilvocarcin aglycones.

8. Oxidative rearrangement processes in the biosynthesis of gilvocarcin V.

9. Biosynthesis of chrysomycins A and B. Origin of the chromophore.

10. The complete gene cluster of the antitumor agent gilvocarcin V and its implication for the biosynthesis of the gilvocarcins.

1. Draft genome of Omphalotus olearius provides a predictive framework for sesquiterpenoid natural product biosynthesis in Basidiomycota.

2. Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties.

3. Roles of the synergistic reductive O-methyltransferase GilM and of O-methyltransferase GilMT in the gilvocarcin biosynthetic pathway.

4. The crystal structure and mechanism of an unusual oxidoreductase, GilR, involved in gilvocarcin V biosynthesis.

5. Cloning and characterization of the ravidomycin and chrysomycin biosynthetic gene clusters.

Review 6. Delineation of gilvocarcin, jadomycin, and landomycin pathways through combinatorial biosynthetic enzymology.

7. Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis.

8. Baeyer-Villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis.

Review 9. Complexity generation during natural product biosynthesis using redox enzymes.

10. Catalytic and structural role of a conserved active site histidine in berberine bridge enzyme.