{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,11]],"date-time":"2026-03-11T02:16:08Z","timestamp":1773195368392,"version":"3.50.1"},"reference-count":17,"publisher":"American Chemical Society (ACS)","issue":"15","license":[{"start":{"date-parts":[[2023,7,20]],"date-time":"2023-07-20T00:00:00Z","timestamp":1689811200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-001"},{"start":{"date-parts":[[2023,7,20]],"date-time":"2023-07-20T00:00:00Z","timestamp":1689811200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-009"},{"start":{"date-parts":[[2023,7,20]],"date-time":"2023-07-20T00:00:00Z","timestamp":1689811200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"}],"funder":[{"DOI":"10.13039\/100000054","name":"National Cancer Institute","doi-asserted-by":"publisher","award":["HHS 75N91019D00024"],"award-info":[{"award-number":["HHS 75N91019D00024"]}],"id":[{"id":"10.13039\/100000054","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. 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Chem."],"published-print":{"date-parts":[[2023,8,4]]},"DOI":"10.1021\/acs.joc.3c00963","type":"journal-article","created":{"date-parts":[[2023,7,20]],"date-time":"2023-07-20T16:58:51Z","timestamp":1689872331000},"page":"10996-11002","source":"Crossref","is-referenced-by-count":9,"title":["Enigmazole Phosphomacrolides from the Marine Sponge <i>Cinachyrella enigmatica<\/i>"],"prefix":"10.1021","volume":"88","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3835-1482","authenticated-orcid":true,"given":"Kentaro","family":"Takada","sequence":"first","affiliation":[{"name":"Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702-1201, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoya","family":"Oku","sequence":"additional","affiliation":[{"name":"Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702-1201, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Megan L.","family":"Peach","sequence":"additional","affiliation":[{"name":"Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702-1201, United States"},{"name":"Basic Science Program, Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702-1201, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tanya T.","family":"Ransom","sequence":"additional","affiliation":[{"name":"Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702-1201, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Curtis J.","family":"Henrich","sequence":"additional","affiliation":[{"name":"Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702-1201, United States"},{"name":"Basic Science Program, Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702-1201, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6821-4943","authenticated-orcid":true,"given":"Kirk R.","family":"Gustafson","sequence":"additional","affiliation":[{"name":"Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702-1201, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2023,7,20]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.111662"},{"key":"ref2\/cit2","doi-asserted-by":"publisher","DOI":"10.3390\/MD19040180"},{"key":"ref3\/cit3","doi-asserted-by":"publisher","DOI":"10.1039\/d1np00078k"},{"key":"ref4\/cit4","doi-asserted-by":"publisher","DOI":"10.1021\/ja1016766"},{"key":"ref5\/cit5","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.1c01179"},{"key":"ref6\/cit6","doi-asserted-by":"publisher","DOI":"10.1139\/v79-517"},{"key":"ref7\/cit7","doi-asserted-by":"publisher","DOI":"10.1021\/ja00499a036"},{"key":"ref8\/cit8","doi-asserted-by":"publisher","DOI":"10.1021\/ja052688r"},{"key":"ref9\/cit9","unstructured":"HMBCcorrelation\nH11\/C7\nwas not observed, indicating no direct evidence of the ether linkage.\nThis assignment was consistent with that obtained by a series of derivatization\nreactions."},{"key":"ref10\/cit10","unstructured":"Apart from the experiment,\nthe modified Mosher\u2019s method was applied to the mono-MTPA ester\nof enigmazole B with the phosphate group protected by methyl groups\n(Figure S4). This experiment demonstrated\nthat two MTPA groups had no serious effect on each other."},{"key":"ref11\/cit11","unstructured":"Finally,\nwe found two\nphosphatases were available for enigmazole B, Antarctic Phosphatase\n(New England Bio. Lab.) and Bacterial phosphatase (Wako)."},{"key":"ref12\/cit12","unstructured":"As\nthe concentration\nof MeOH decreased, the yield of undesirable hydrolysate (M + 2 OH)\nincreases. The experiment using deuterated reagents (NaOD \/ CD3OD)\nrevealed that unsaturated carboxylic acid is more readily remethylated\nthan the other carboxylic acid."},{"key":"ref13\/cit13","doi-asserted-by":"publisher","DOI":"10.1021\/ja00775a068"},{"key":"ref14\/cit14","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b02684"},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1111\/j.1747-0285.2007.00508.x"},{"key":"ref16\/cit16","doi-asserted-by":"publisher","DOI":"10.3390\/molecules15074526"},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1002\/1096-987X(20010115)22:1<21::AID-JCC3>3.0.CO;2-I"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.3c00963","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.3c00963","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,4]],"date-time":"2023-08-04T08:43:21Z","timestamp":1691138601000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.3c00963"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,20]]},"references-count":17,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2023,8,4]]}},"alternative-id":["10.1021\/acs.joc.3c00963"],"URL":"https:\/\/doi.org\/10.1021\/acs.joc.3c00963","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,20]]}}}