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As configurational assignment proved difficult, a bioinformatic analysis of the biosynthetic gene cluster was chosen to predict the configuration of each stereocenter. In\u2010depth analysis of the corresponding biosynthetic proteins established a hybrid polyketide synthase\/nonribosomal peptide synthetase origin of haprolid and allowed for stereochemical assignments. A subsequent total synthesis yielded haprolid and corroborated all predictions made. Intriguingly, haprolid showed cytotoxicity against several cell lines in the nanomolar range whereas other cells were almost unaffected by treatment with the compound.<\/jats:p>","DOI":"10.1002\/anie.201603288","type":"journal-article","created":{"date-parts":[[2016,7,12]],"date-time":"2016-07-12T13:06:42Z","timestamp":1468328802000},"page":"10113-10117","source":"Crossref","is-referenced-by-count":25,"title":["Isolation, Structure Elucidation, and (Bio)Synthesis of Haprolid, a Cell\u2010Type\u2010Specific Myxobacterial Cytotoxin"],"prefix":"10.1002","volume":"55","author":[{"given":"Heinrich","family":"Steinmetz","sequence":"first","affiliation":[{"name":"Helmholtz Center for Infection Research (HZI) Department Microbial Drugs  Inhoffenstrasse 7 38124 Braunschweig Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun","family":"Li","sequence":"additional","affiliation":[{"name":"Institute for Organic Chemistry Gottfried Leibniz Universit\u00e4t 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