Direct formation of chromopyrrolic acid from indole-3-pyruvic acid by StaD, a novel hemoprotein in indolocarbazole biosynthesis

Tetrahedron Letters

Volumn 47, Issue 4, 2006, Pages 473-475

  Asamizu, Shumpei ^a   Kato, Yasuo ^a   Igarashi, Yasuhiro ^a   Furumai, Tamotsu ^a   Onaka, Hiroyasu ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Biosynthesis; Chromopyrrolic acid; Heme; Indole 3 pyruvic acid; Indolocarbazole; RebD; StaD; Staurosporine; VioB

Indexed keywords

ACID; CARBAZOLE DERIVATIVE; CHROMOPYRROLIC ACID; HEMOPROTEIN; INDOLE DERIVATIVE; INDOLEPYRUVIC ACID; PROTEIN STAD; PYRROLE DERIVATIVE; STAUROSPORINE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CHEMICAL REACTION; METHODOLOGY; STREPTOMYCES;

STREPTOMYCES; STREPTOMYCES SP.;

EID: 29144525471     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.061     Document Type: Article

References (13)

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6. 2 was changed into NdeI site by QuikChange site-directed mutagenesis kit (Stratagene) with the two following primers: StaD-Nde-sense, 5′-CAGGTCGAAGACGCTCATATGGACCGGTCCGAGCGGC-3′; StaD-Nde-anti, 5′-GCCGCTCGGACCGGTCCATATGAGCGTCTTCGACCTG-3′. The mutated plasmid was digested with NdeI and HindIII, and the resulting fragment was inserted between the NdeI and HindIII sites of pET26b(+) (Novagen) to generate pETStaDN. The C-terminal of StaD is amplified by using PCR with the following primers: StaD-C-up, 5′-TGATGACGGGCCTGATGCGGCCGCTGGCGG-3′; StaD-C-Xho, 5′-CCGGCTCGAGCGGCTCGGCGGGCGGAAGTGGTCGGCCCAG-3′. The amplified 257 bp fragment was inserted between the NotI and XhoI sites of pETStaDN to generate pETStaD.
7. 600 = 0.6, 100 μM IPTG and l-arabinose (1 mg/ml) were added to induce StaD and chaperones, and grown for an additional 15 h.
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9. 4Cl were incubated at 30°C for 5 min in 100 mM sodium phosphate buffer (pH 7.0). The amount of reaction product (chromopyrrolic acid) was estimated from the area of HPLC elution profile.
10. 3COOH (pH 3.5) detected at 254 nm. The collected fractions were combined and were lyophilized for NMR analysis.
11. +: m/z = 386.1.
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