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The emergence of daptomycin\u2010resistant bacterial strains has renewed interest in generating daptomycin analogs. Previous studies have shown that replacing the tryptophan of daptomycin with aromatic groups can generate analogs with enhanced potency. Additionally, we have demonstrated that aromatic prenyltransferases can attach diverse groups to the tryptophan of daptomycin. Here, we report the use of the prenyltransferase CdpNPT to derivatize the tryptophan of daptomycin with a library of benzylic and heterocyclic pyrophosphates. An analytical\u2010scale study revealed that CdpNPT can transfer various aromatic groups onto daptomycin. Subsequent scaled\u2010up and purified reactions indicated that the enzyme can attach aromatic groups to <jats:italic>N<\/jats:italic>1, <jats:italic>C<\/jats:italic>2, <jats:italic>C<\/jats:italic>5 and <jats:italic>C<\/jats:italic>6 positions of Trp1 of daptomycin. In vitro antibacterial activity assays using six of these purified compounds identified aromatic substituted daptomycin analogs show potency against both daptomycin\u2010susceptible and resistant strains of Gram\u2010positive bacteria. These findings suggest that installing aromatic groups on the Trp1 of daptomycin can lead to the generation of potent daptomycin analogs.<\/jats:p>","DOI":"10.1002\/cbic.202400503","type":"journal-article","created":{"date-parts":[[2024,7,17]],"date-time":"2024-07-17T22:15:28Z","timestamp":1721254528000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Chemoenzymatic Modification of Daptomycin: Aromatic Group Installation on Trp1"],"prefix":"10.1002","volume":"25","author":[{"given":"Dustin A.","family":"Dimas","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Oklahoma  Stephenson Life Sciences Research Center, 101 Stephenson Parkway Norman, Oklahoma 73019 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vikas","family":"Kumar","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Oklahoma  Stephenson Life Sciences Research Center, 101 Stephenson Parkway Norman, Oklahoma 73019 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Prashant S.","family":"Mandal","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Oklahoma  Stephenson Life Sciences Research Center, 101 Stephenson Parkway Norman, Oklahoma 73019 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Johanna M.","family":"Masterson","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Oklahoma  Stephenson Life Sciences Research Center, 101 Stephenson Parkway Norman, Oklahoma 73019 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marco","family":"Tonelli","sequence":"additional","affiliation":[{"name":"National Magnetic Resonance Facility at Madison University of Wisconsin-Madison  411 Babcock Drive Madison, Wisconsin 45005 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0960-4794","authenticated-orcid":false,"given":"Shanteri","family":"Singh","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Oklahoma  Stephenson Life Sciences Research Center, 101 Stephenson Parkway Norman, Oklahoma 73019 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,9,9]]},"reference":[{"key":"e_1_2_9_1_1","unstructured":"\u00a0"},{"key":"e_1_2_9_2_2","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/dkh546"},{"key":"e_1_2_9_3_2","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/46.4.523"},{"key":"e_1_2_9_4_2","doi-asserted-by":"publisher","DOI":"10.1086\/653519"},{"key":"e_1_2_9_5_2","doi-asserted-by":"publisher","DOI":"10.1093\/cid\/cit112"},{"key":"e_1_2_9_6_2","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/dkq087"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.40.761"},{"key":"e_1_2_9_8_1","unstructured":"\u00a0"},{"key":"e_1_2_9_9_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.41.1093"},{"key":"e_1_2_9_10_2","first-page":"1507","volume":"151","author":"Miao V.","year":"2005","journal-title":"Access Microbiol."},{"key":"e_1_2_9_11_1","unstructured":"\u00a0"},{"key":"e_1_2_9_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamem.2011.01.001"},{"key":"e_1_2_9_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemphyslip.2008.04.004"},{"key":"e_1_2_9_14_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.47.8.2538-2544.2003"},{"key":"e_1_2_9_15_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.35.11.2282"},{"key":"e_1_2_9_16_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.01410-07"},{"key":"e_1_2_9_17_2","doi-asserted-by":"publisher","DOI":"10.1128\/JB.00011-12"},{"key":"e_1_2_9_18_2","doi-asserted-by":"publisher","DOI":"10.1038\/emboj.2009.129"},{"key":"e_1_2_9_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2016.05.052"},{"key":"e_1_2_9_20_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1600321113"},{"key":"e_1_2_9_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsinfecdis.7b00138"},{"key":"e_1_2_9_22_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M114.554444"},{"key":"e_1_2_9_23_2","doi-asserted-by":"publisher","DOI":"10.3390\/antibiotics9010017"},{"key":"e_1_2_9_24_2","doi-asserted-by":"publisher","DOI":"10.1101\/cshperspect.a026997"},{"key":"e_1_2_9_25_1","unstructured":"\u00a0"},{"key":"e_1_2_9_26_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.00023-18"},{"key":"e_1_2_9_27_2","first-page":"391","volume":"30","author":"Casanova N. 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