Naphthyridinomycin
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| Category | Antibiotics |
| Catalog number | BBF-01992 |
| CAS | 54913-26-7 |
| Molecular Weight | 417.45 |
| Molecular Formula | C21H27N3O6 |
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Description
Naphthyridinomycin is an antibiotic produced by Str. lusitanus AYB-1026. It has anti-gram-positive bacteria and gram-positive bacteria activity.
Specification
| Synonyms | Naphthyridinomycin A |
| IUPAC Name | (1R,3R,4S,9S,16S,18S,19S,21R)-21-hydroxy-16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-5-oxa-8,17,20-triazahexacyclo[15.3.1.03,19.04,8.09,18.010,15]henicosa-10(15),12-diene-11,14-dione |
| Canonical SMILES | CC1=C(C(=O)C2=C(C1=O)C3C4C5C(CC(N5C)C(N4C2CO)O)C6N3CCO6)OC |
| InChI | InChI=1S/C21H27N3O6/c1-8-17(26)13-12(18(27)19(8)29-3)11(7-25)24-16-14-9(6-10(20(24)28)22(14)2)21-23(15(13)16)4-5-30-21/h9-11,14-16,20-21,25,28H,4-7H2,1-3H3/t9-,10-,11-,14+,15+,16+,20-,21+/m1/s1 |
| InChI Key | SXDWNOFDSOXRRM-ZNKNALJYSA-N |
Properties
| Appearance | Red Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 663.5±55.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Methanol, Ether, water |
Reference Reading
1. Biosynthesis of Tetrahydroisoquinoline Antibiotics
Gong-Li Tang, Man-Cheng Tang, Li-Qiang Song, Yue Zhang Curr Top Med Chem. 2016;16(15):1717-26. doi: 10.2174/1568026616666151012112329.
The tetrahydroisoquinoline (THIQ) alkaloids are naturally occurring antibiotics isolated from a variety of microorganisms and marine invertebrates. This family of natural products exhibit broad spectrum antimicrobial and strong antitumor activities, and the potency of clinical application has been validated by the marketing of ecteinascidin 743 (ET-743) as anticancer drug. In the past 20 years, the biosynthetic gene cluster of six THIQ antibiotics has been characterized including saframycin Mx1 from Myxococcus xanthus, safracin-B from Pseudomonas fluorescens, saframycin A, naphthyridinomycin, and quinocarcin from Streptomyces, as well as ET-743 from Ecteinascidia turbinata. This review gives a brief summary of the current status in understanding the molecular logic for the biosynthesis of these natural products, which provides new insights on the biosynthetic machinery involved in the nonribosomal peptide synthetase system. The proposal of the THIQ biosynthetic pathway not only shows nature's route to generate such complex molecules, but also set the stage to develop a different process for production of ET-743 by synthetic biology.
2. Naphthyridinomycin biosynthesis revealing the use of leader peptide to guide nonribosomal peptide assembly
Jin-Yue Pu, Chao Peng, Man-Cheng Tang, Yue Zhang, Jian-Ping Guo, Li-Qiang Song, Qiang Hua, Gong-Li Tang Org Lett. 2013 Jul 19;15(14):3674-7. doi: 10.1021/ol401549y. Epub 2013 Jul 10.
Analysis of naphthyridinomycin gene cluster revealed that this antibiotic is generated by nonribosomal peptide synthetase (NRPS) machinery. However, four modules encoded by two genes do not correspond with the structural units in the final product. Genetic and biochemical characterization of the gene cluster suggested that the leader peptide mechanism for the NRPS assembly line was involved in biosynthesis of this tetrahydroisoquinoline alkaloid.
3. Extracellularly oxidative activation and inactivation of matured prodrug for cryptic self-resistance in naphthyridinomycin biosynthesis
Yue Zhang, Wan-Hong Wen, Jin-Yue Pu, Man-Cheng Tang, Liwen Zhang, Chao Peng, Yuquan Xu, Gong-Li Tang Proc Natl Acad Sci U S A. 2018 Oct 30;115(44):11232-11237. doi: 10.1073/pnas.1800502115. Epub 2018 Oct 16.
Understanding how antibiotic-producing bacteria deal with highly reactive chemicals will ultimately guide therapeutic strategies to combat the increasing clinical resistance crisis. Here, we uncovered a distinctive self-defense strategy featured by a secreted oxidoreductase NapU to perform extracellularly oxidative activation and conditionally overoxidative inactivation of a matured prodrug in naphthyridinomycin (NDM) biosynthesis from Streptomyces lusitanus NRRL 8034. It was suggested that formation of NDM first involves a nonribosomal peptide synthetase assembly line to generate a prodrug. After exclusion and prodrug maturation, we identified a pharmacophore-inactivated intermediate, which required reactivation by NapU via oxidative C-H bond functionalization extracellularly to afford NDM. Beyond that, NapU could further oxidatively inactivate the NDM pharmacophore to avoid self-cytotoxicity if they coexist longer than necessary. This discovery represents an amalgamation of sophisticatedly temporal and spatial shielding mode conferring self-resistance in antibiotic biosynthesis from Gram-positive bacteria.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
