Peptide name : Phenyloxazoline synthase MbtB (Mycobactin synthetase protein B)

Source/Organism : NRRL B-24137T strain, Saharan soil, Algeria

Linear/Cyclic : Not found

Chirality : Not found

Peptide length: 1044

C-terminal modification: Not found

N-terminal modification : Not found

Non-natural peptide information: None

Assay type : Not specified

Assay time : Not found

Activity : Not found

Cell line : Not found

Cancer type : Not found

Other activity : Not found

Amino acid composition bar chart :

Molecular mass : 113726.987 Dalton

Aliphatic index : 0.938

Instability index : 39.6512

Hydrophobicity (GRAVY) : -0.162

Isoelectric point : 5.0535

Charge (pH 7) : -46.6581

Aromaticity : 0.069

Molar extinction coefficient (cysteine, cystine): (139800, 140050)

Hydrophobic/hydrophilic ratio : 1.35665914

hydrophobic moment : 0.0114

Missing amino acid : None

Most occurring amino acid : A

Most occurring amino acid frequency : 118

Least occurring amino acid : C

Least occurring amino acid frequency : 4

Secondary structure fraction (Helix, Turn, Sheet): (0.3, 0.3, 0.3)

SMILES Notation: 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1 : Huang S, et al. Identification and characterization of the biosynthetic gene cluster of thiolutin, a tumor angiogenesis inhibitor, in Saccharothrix algeriensis NRRL B-24137. Anticancer Agents Med Chem. 2015; 15:277-84. doi: 10.2174/1871520614666141027145200

Paper title : Identification and characterization of the biosynthetic gene cluster of thiolutin, a tumor angiogenesis inhibitor, in Saccharothrix algeriensis NRRL B-24137.

Doi : https://doi.org/10.2174/1871520614666141027145200

Abstract : In this study, a new dithiolopyrrolone biosynthetic pathway was identified in Saccharothrix algeriensis NRRL B-24137, which was reported to produce a variety of dithiolopyrrolone natural products including thiolutin, a potential drug candidate for tumor angiogenesis inhibition. Bioinformatics analysis of the cluster revealed that it contains all the essential genes for holothin core biosynthesis and several other auxiliary genes. Interestingly, heterologous expression of the gene cluster in Streptomyces albus only induced the production of holomycin, implying that the gene responsible for the N4-methylation and the gene(s) involved in the formation of various acylated chains on N7 position of the holothin may locate outside the gene cluster. Incubation of holomycin with S-adenosyl-L-methionine (SAM) in the cell-free extract of Sa. algeriensis resulted in the production of thiolutin, suggesting that the N4-methyl group of thiolutin is originated from SAM, and the N4-methylation could be in the late stage of biosynthesis of thiolutin type dithiolopyrrolones. An evolution-based model for biosynthesis of thiolutin and its analogs was further proposed based on these results.