天然产物杰多霉素家族的生物合成与全合成研究
Biosynthesis and Total Synthesis Studies on The Jadomycin Family of Natural Products.
作者信息
Sharif Ehesan U, O'Doherty George A
机构信息
Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA, 02115, Homepage: http://nuweb9.neu.edu/odoherty/
出版信息
European J Org Chem. 2012 Apr;2012(11). doi: 10.1002/ejoc.201101609.
Abstract
Jadomycins are unique angucycline polyketides, which are produced by soil bacteria under specific nutrient and environmental conditions. Their unique structural complexity and biological activities have engendered extensive study of the jadomycin class of natural compounds in terms of biological activity, biosynthesis, and synthesis. This review outlines the recent developments in the study of the synthesis and biosynthesis of jadomycins.
摘要
杰多霉素是一类独特的安古霉素聚酮化合物，由土壤细菌在特定的营养和环境条件下产生。它们独特的结构复杂性和生物活性促使人们对杰多霉素类天然化合物在生物活性、生物合成和合成方面进行了广泛研究。本综述概述了杰多霉素合成和生物合成研究的最新进展。
相似文献
1
Biosynthesis and Total Synthesis Studies on The Jadomycin Family of Natural Products.天然产物杰多霉素家族的生物合成与全合成研究
European J Org Chem. 2012 Apr;2012(11). doi: 10.1002/ejoc.201101609.
2
Biosynthesis, synthetic studies, and biological activities of the jadomycin alkaloids and related analogues.制霉素生物碱及相关类似物的生物合成、合成研究和生物活性。
Alkaloids Chem Biol. 2020;84:125-199. doi: 10.1016/bs.alkal.2020.02.001. Epub 2020 Mar 9.
3
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.杰多霉素B双脱氧糖组分的生物合成：委内瑞拉链霉菌ISP5230的杰多霉素基因簇中负责L-洋地黄毒糖组装并将其转移至安古霉素苷元的基因。
Microbiology (Reading). 2002 Apr;148(Pt 4):1091-1103. doi: 10.1099/00221287-148-4-1091.
4
Synthesis and in Vitro Cytotoxicity Evaluation of Jadomycins.金霉素类的合成及体外细胞毒性评价。
Chem Pharm Bull (Tokyo). 2023;71(9):730-733. doi: 10.1248/cpb.c23-00351.
5
ISP5230 Maintains Excretion of Jadomycin upon Disruption of the MFS Transporter JadL Located within the Natural Product Biosynthetic Gene Cluster.当位于天然产物生物合成基因簇内的主要易化子超家族（MFS）转运蛋白JadL被破坏时，ISP5230维持制霉菌素的排泄。
Front Microbiol. 2017 Mar 21;8:432. doi: 10.3389/fmicb.2017.00432. eCollection 2017.
6
Jadomycins derived from the assimilation and incorporation of norvaline and norleucine.来源于正缬氨酸和正亮氨酸同化和掺入的绛霉素。
J Nat Prod. 2011 Nov 28;74(11):2420-4. doi: 10.1021/np200689w. Epub 2011 Nov 3.
7
Eight-membered ring-containing jadomycins: implications for non-enzymatic natural products biosynthesis.含八元环的柔红霉素：对非酶天然产物生物合成的启示。
J Am Chem Soc. 2015 Mar 11;137(9):3271-5. doi: 10.1021/ja5114672. Epub 2015 Feb 26.
8
Jadomycin breast cancer cytotoxicity is mediated by a copper-dependent, reactive oxygen species-inducing mechanism.杰达霉素诱导乳腺癌细胞毒性是通过铜依赖性的活性氧诱导机制介导的。
Pharmacol Res Perspect. 2015 Mar;3(2):e00110. doi: 10.1002/prp2.110.
9
Isolation and Synthetic Diversification of Jadomycin 4-Amino-l-phenylalanine.制霉菌素4-氨基-L-苯丙氨酸的分离与合成多样化
J Nat Prod. 2015 Jun 26;78(6):1208-14. doi: 10.1021/np5009398. Epub 2015 Jun 2.
10
The dynamic structure of jadomycin B and the amino acid incorporation step of its biosynthesis.杰多霉素B的动态结构及其生物合成中的氨基酸掺入步骤。
J Am Chem Soc. 2004 Apr 14;126(14):4496-7. doi: 10.1021/ja031724o.
引用本文的文献
1
asymmetric Achmatowicz approach to oligosaccharide natural products.不对称 Achmatowicz 方法用于寡糖天然产物。
Chem Commun (Camb). 2022 Nov 22;58(93):12913-12926. doi: 10.1039/d2cc05280f.
2
Himalaquinones A-G, Angucyclinone-Derived Metabolites Produced by the Himalayan Isolate sp. PU-MM59.喜马拉醌 A-G，由喜马拉雅分离株 sp. PU-MM59 产生的蒽环酮衍生代谢物。
J Nat Prod. 2021 Jul 23;84(7):1930-1940. doi: 10.1021/acs.jnatprod.1c00192. Epub 2021 Jun 25.
3
Targeted Genome Mining-From Compound Discovery to Biosynthetic Pathway Elucidation.靶向基因组挖掘——从化合物发现到生物合成途径阐明
Microorganisms. 2020 Dec 19;8(12):2034. doi: 10.3390/microorganisms8122034.
4
Ru-catalyzed sequence for the synthesis of cyclic amido-ethers.用于合成环状酰胺醚的钌催化序列
Chem Sci. 2017 Jan 1;8(1):770-774. doi: 10.1039/c6sc02849g. Epub 2016 Sep 12.
5
A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides.2,3-二脱氧己-2-烯吡喃糖苷近期合成应用综述。
Molecules. 2015 May 8;20(5):8357-94. doi: 10.3390/molecules20058357.
6
Merremoside D: de novo synthesis of the purported structure, NMR analysis, and comparison of spectral data.莫雷罗苷 D：推测结构的从头合成、NMR 分析和光谱数据比较。
Org Lett. 2014 Jan 17;16(2):492-5. doi: 10.1021/ol403369h. Epub 2013 Dec 19.
本文引用的文献
1
Jadomycins derived from the assimilation and incorporation of norvaline and norleucine.来源于正缬氨酸和正亮氨酸同化和掺入的绛霉素。
J Nat Prod. 2011 Nov 28;74(11):2420-4. doi: 10.1021/np200689w. Epub 2011 Nov 3.
2
Copper-mediated nuclease activity of jadomycin B.金霉素 B 的铜介导的核酸酶活性。
Bioorg Med Chem. 2011 Jun 1;19(11):3357-60. doi: 10.1016/j.bmc.2011.04.043. Epub 2011 Apr 29.
3
Genome-wide analysis of the role of GlnR in Streptomyces venezuelae provides new insights into global nitrogen regulation in actinomycetes.全基因组分析 GlnR 在委内瑞拉链霉菌中的作用为放线菌全局氮调控提供新视角。
BMC Genomics. 2011 Apr 4;12:175. doi: 10.1186/1471-2164-12-175.
4
Total synthesis of jadomycin A and a carbasugar analogue of jadomycin B.jadomycin A 的全合成及 jadomycin B 的碳环糖类似物。
Angew Chem Int Ed Engl. 2010 Dec 3;49(49):9492-5. doi: 10.1002/anie.201005329.
5
Characterization of JadH as an FAD- and NAD(P)H-dependent bifunctional hydroxylase/dehydrase in jadomycin biosynthesis.JadH作为制霉素生物合成中一种依赖FAD和NAD(P)H的双功能羟化酶/脱水酶的特性分析。
Chembiochem. 2010 May 17;11(8):1055-60. doi: 10.1002/cbic.201000178.
6
Discovery of unique lanthionine synthetases reveals new mechanistic and evolutionary insights.发现独特的羊毛硫氨酸合成酶揭示了新的机制和进化见解。
PLoS Biol. 2010 Mar 23;8(3):e1000339. doi: 10.1371/journal.pbio.1000339.
7
Diverse DNA-cleaving capacities of the jadomycins through precursor-directed biosynthesis.通过前体定向生物合成实现的节杆菌霉素多样化的 DNA 切割能力。
Org Lett. 2010 Mar 19;12(6):1172-5. doi: 10.1021/ol902907r.
8
Antimicrobial activities of jadomycin B and structurally related analogues.杰多霉素B及结构相关类似物的抗菌活性
Antimicrob Agents Chemother. 2009 Mar;53(3):1245-7. doi: 10.1128/AAC.00801-08. Epub 2008 Dec 15.
9
Jadomycin B, an Aurora-B kinase inhibitor discovered through virtual screening.贾多霉素B，一种通过虚拟筛选发现的极光激酶B抑制剂。
Mol Cancer Ther. 2008 Aug;7(8):2386-93. doi: 10.1158/1535-7163.MCT-08-0035.
10
Synthesis of carbasugar C-1 phosphates via Pd-catalyzed cyclopropanol ring opening.通过钯催化的环丙醇开环反应合成碳环糖C-1磷酸酯。
Org Lett. 2008 Aug 21;10(16):3381-4. doi: 10.1021/ol801106r. Epub 2008 Jul 18.
Zotero 插件