title: Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis.
abstract: Covering: 1997 to 2010. The angucycline group is the largest group of type II PKS-engineered natural products, rich in biological activities and chemical scaffolds. This stimulated synthetic creativity and biosynthetic inquisitiveness. The synthetic studies used five different strategies, involving Diels-Alder reactions, nucleophilic additions, electrophilic additions, transition-metal mediated cross-couplings and intramolecular cyclizations to generate the angucycline frames. Biosynthetic studies were particularly intriguing when unusual framework rearrangements by post-PKS tailoring oxidoreductases occurred, or when unusual glycosylation reactions were involved in decorating the benz[a]anthracene-derived cores. This review follows our previous reviews, which were published in 1992 and 1997, and covers new angucycline group antibiotics published between 1997 and 2010. However, in contrast to the previous reviews, the main focus of this article is on new synthetic approaches and biosynthetic investigations, most of which were published between 1997 and 2010, but go beyond, e.g. for some biosyntheses all the way back to the 1980s, to provide the necessary context of information.
authors.affiliation: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, 789 S. Limestone Street, Lexington, Kentucky 40536-0596, USA.
authors.forename: Madan K
authors.initials: MK
authors.lastname: Kharel
authors.forename: Pallab
authors.initials: P
authors.lastname: Pahari
authors.forename: Micah D
authors.initials: MD
authors.lastname: Shepherd
authors.forename: Nidhi
authors.initials: N
authors.lastname: Tibrewal
authors.forename: S Eric
authors.initials: SE
authors.lastname: Nybo
authors.forename: Khaled A
authors.initials: KA
authors.lastname: Shaaban
authors.forename: Jürgen
authors.initials: J
authors.lastname: Rohr
mesh_terms: D000617:Aminoglycosides / Q000096:biosynthesis* / Q000138:chemical synthesis / Q000494:pharmacology; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000138:chemical synthesis* / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000494:pharmacology; D053898:Biosynthetic Pathways; D002240:Carbohydrate Sequence; D045744:Cell Line, Tumor; D003374:Coumarins / Q000138:chemical synthesis / Q000494:pharmacology; D006027:Glycosides / Q000096:biosynthesis / Q000138:chemical synthesis / Q000494:pharmacology; D006031:Glycosylation; D006801:Humans; D007546:Isoquinolines / Q000737:chemistry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry; D009369:Neoplasms / Q000188:drug therapy; D061065:Polyketides / Q000138:chemical synthesis / Q000494:pharmacology; D011809:Quinones / Q000737:chemistry; D013302:Streptomyces; D013329:Structure-Activity Relationship; D000095602:Angucyclines and Angucyclinones
chemical_list: D000617:Aminoglycosides; D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D001688:Biological Products; D003374:Coumarins; D006027:Glycosides; D007546:Isoquinolines; D009285:Naphthoquinones; D061065:Polyketides; D011809:Quinones; C510997:angucyclinone; C506597:jadomycin A; C113593:landomycin E; C064648:landomycin A; C072147:hatomarubigin A; C081750:jadomycin B; C001507:kinamycin A; D000095602:Angucyclines and Angucyclinones; C059021:kinamycin F; C038314:ravidomycin; C031781:gilvocarcin V; C035075:chrysomycin A; C036275:chrysomycin B