Chemistry:Jadomycin

From HandWiki
Jadomycin B
Jadomycin B.png
Names
Other names
Jadomycin L-isoleucine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
Properties
C30H31NO9
Molar mass 549.576 g·mol−1
Appearance Deep red-purple solid
Solubility Soluble in various organic solvents[vague]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

A jadomycin is a natural product produced by Streptomyces venezuelae ISP5230 (ATCC10712[1]), the organism which is most well known for making the antibiotic chloramphenicol. The name jadomycin is applied to a family of related angucyclines which are distinguished by the E ring (usually an oxoazolone ring), which is derived from an amino acid. The amino acid incorporation which forms the E-ring is a chemical reaction, rather than enzymatic, an uncommon occurrence in biosynthesis. As such a number of jadomycins incorporating different amino acids have been discovered. Jadomycin A was the first compound of this family to be isolated and constitutes the angucylic backbone with L-isoleucine incorporated into the E-ring.[2] A related analog, jadomycin B, is modified by glycosylation with a 2,6-dideoxy sugar, L-digitoxose.[3] Jadomycins have cytotoxic and antibacterial properties.

Biosynthesis

The jadomycin biosynthetic gene cluster is well characterized. Jadomycin biosynthesis encompasses type II polyketide synthase (T2Pks) assembly to generate the angucycline component,[4] and a dideoxy sugar pathway, to generate the sugar donor NDP-L-digitoxose.[5] Studies have implicated JadG, an FAD-dependent oxygenase, in the ring cleavage required for incorporation of amino acids.[6] JadS, the glycosyltransferase that transfers L-digitoxose, has been shown to be flexible with respect to the sugar donor.[7][8][9]

Analogs based on E-ring modification

Jadomycin analogs have been obtained through culture of S. venezuelae in the presence of a single amino acid. The diversity of jadomycins includes those incorporating naturally occurring amino acids,[10] non-proteinogenic amino acids,[11][12] and synthetic amino acids with handles enabling further chemical modification.[13][14]

References

  1. ↑ "Streptomyces venezuelae Ehrlich et al. ATCC ® 10712™" (in en). https://www.atcc.org/products/all/10712.aspx. 
  2. ↑ Ayer, Stephen W.; McInnes, A. Gavin; Thibault, Pierre; Walter, John A.; Doull, Janice L.; Parnell, Tracy; Vining, Leo C. (1991-10-28). "Jadomycin, a novel 8H-benz[b]oxazolo[3,2-f]phenanthridine antibiotic from streptomyces venezuelae ISP5230.". Tetrahedron Letters 32 (44): 6301–6304. doi:10.1016/0040-4039(91)80152-V. 
  3. ↑ DOULL, JANICE L.; AYER, STEPHEN W.; SINGH, AMRIT K.; THIBAULT, PIERRE (1993-05-25). "Production of a novel polyketide antibiotic, jadomycin B, by Streptomyces venezuelae following heat shock." (in en). The Journal of Antibiotics 46 (5): 869–871. doi:10.7164/antibiotics.46.869. ISSN 0021-8820. PMID 8514643. 
  4. ↑ Han, Lei; Yang, Keqian; Ramalingam, Eswar; Mosher, Roy H.; Vining, Leo C. (1994). "Cloning and characterization of polyketide synthase genes for jadomycin B biosynthesis in Streptomyces venezuelae ISP5230". Microbiology 140 (12): 3379–3389. doi:10.1099/13500872-140-12-3379. PMID 7881555. 
  5. ↑ Wang, Liru; White, Robert L.; Vining, Leo C. (2002). "Biosynthesis of the dideoxysugar component of jadomycin B: genes in the jad cluster of Streptomyces venezuelae ISP5230 for l-digitoxose assembly and transfer to the angucycline aglycone". Microbiology 148 (4): 1091–1103. doi:10.1099/00221287-148-4-1091. PMID 11932454. 
  6. ↑ Tibrewal, Nidhi; Pahari, Pallab; Wang, Guojun; Kharel, Madan K.; Morris, Caleb; Downey, Theresa; Hou, Yanpeng; Bugni, Tim S. et al. (2012). "Baeyer–Villiger C–C Bond Cleavage Reaction in Gilvocarcin and Jadomycin Biosynthesis" (in en). Journal of the American Chemical Society 134 (44): 18181–18184. doi:10.1021/ja3081154. PMID 23102024. 
  7. ↑ Jakeman, David L.; Borissow, Charles N.; Graham, Cathy L.; Timmons, Shannon C.; Reid, Taryn R.; Syvitski, Ray T. (2006-08-29). "Substrate flexibility of a 2,6-dideoxyglycosyltransferase" (in en). Chemical Communications (35): 3738–3740. doi:10.1039/B608847C. ISSN 1364-548X. PMID 17047829. 
  8. ↑ Forget, S. M.; Na, Jungwook; McCormick, N. E.; Jakeman, D. L. (2017-03-28). "Biosynthetic 4,6-dehydratase gene deletion: isolation of a glucosylated jadomycin natural product provides insight into the substrate specificity of glycosyltransferase JadS" (in en). Organic & Biomolecular Chemistry 15 (13): 2725–2729. doi:10.1039/C7OB00259A. ISSN 1477-0539. PMID 28291274. 
  9. ↑ Li, Liyuan; Pan, Guohui; Zhu, Xifen; Fan, Keqiang; Gao, Wubin; Ai, Guomin; Ren, Jinwei; Shi, Mingxin et al. (2017-04-20). "Engineered jadomycin analogues with altered sugar moieties revealing JadS as a substrate flexible O-glycosyltransferase" (in en). Applied Microbiology and Biotechnology 101 (13): 5291–5300. doi:10.1007/s00253-017-8256-y. ISSN 0175-7598. PMID 28429060. 
  10. ↑ Jakeman, David L.; Farrell, Spring; Young, Wendy; Doucet, René J.; Timmons, Shannon C. (2005-03-01). "Novel jadomycins: incorporation of non-natural and natural amino acids". Bioorganic & Medicinal Chemistry Letters 15 (5): 1447–1449. doi:10.1016/j.bmcl.2004.12.082. PMID 15713404. 
  11. ↑ Jakeman, David L.; Graham, Cathy L.; Reid, Taryn R. (2005-12-01). "Novel and expanded jadomycins incorporating non-proteogenic amino acids". Bioorganic & Medicinal Chemistry Letters 15 (23): 5280–5283. doi:10.1016/j.bmcl.2005.08.047. PMID 16185863. 
  12. ↑ Forget, Stephanie M.; Robertson, Andrew W.; Overy, David P.; Kerr, Russell G.; Jakeman, David L. (2017-05-18). "Furan and Lactam Jadomycin Biosynthetic Congeners Isolated from Streptomyces venezuelae ISP5230 Cultured with Nε-Trifluoroacetyl-l-lysine". Journal of Natural Products 80 (6): 1860–1866. doi:10.1021/acs.jnatprod.7b00152. ISSN 0163-3864. PMID 28520425. 
  13. ↑ Dupuis, Stephanie N.; Robertson, Andrew W.; Veinot, Thomas; Monro, Susan M. A.; Douglas, Susan E.; Syvitski, Ray T.; Goralski, Kerry B.; McFarland, Sherri A. et al. (2012-04-02). "Synthetic diversification of natural products: semi-synthesis and evaluation of triazole jadomycins" (in en). Chemical Science 3 (5): 1640. doi:10.1039/C2SC00663D. ISSN 2041-6539. http://pubs.rsc.org/-/content/articlehtml/2012/sc/c2sc00663d. 
  14. ↑ Robertson, Andrew W.; Martinez-Farina, Camilo F.; Smithen, Deborah A.; Yin, Huimin; Monro, Susan; Thompson, Alison; McFarland, Sherri A.; Syvitski, Raymond T. et al. (2015). "Eight-Membered Ring-Containing Jadomycins: Implications for Non-enzymatic Natural Products Biosynthesis" (in en). Journal of the American Chemical Society 137 (9): 3271–3275. doi:10.1021/ja5114672. PMID 25692677. https://nrc-publications.canada.ca/eng/view/accepted/?id=565aaf4c-202c-4bd1-9904-0c961a34c2e4. 



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