{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T09:41:44Z","timestamp":1785922904897,"version":"3.56.0"},"reference-count":73,"publisher":"Oxford University Press (OUP)","issue":"1","license":[{"start":{"date-parts":[[2024,5,6]],"date-time":"2024-05-06T00:00:00Z","timestamp":1714953600000},"content-version":"vor","delay-in-days":126,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["92251306"],"award-info":[{"award-number":["92251306"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2020YFA0608300"],"award-info":[{"award-number":["2020YFA0608300"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]},{"name":"NSFC project","award":["42188102"],"award-info":[{"award-number":["42188102"]}]},{"name":"NSFC project","award":["42276120"],"award-info":[{"award-number":["42276120"]}]},{"name":"International Science Partnership Program of the Chinese Academy of Sciences","award":["121311KYSB20190029"],"award-info":[{"award-number":["121311KYSB20190029"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2024,1,8]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Chirality, a fundamental property of matter, is often overlooked in the studies of marine organic matter cycles. Dihydroxypropanesulfonate (DHPS), a globally abundant organosulfur compound, serves as an ecologically important currency for nutrient and energy transfer from phytoplankton to bacteria in the ocean. However, the chirality of DHPS in nature and its transformation remain unclear. Here, we developed a novel approach using chiral phosphorus-reagent labeling to separate DHPS enantiomers. Our findings demonstrated that at least one enantiomer of DHPS is present in marine diatoms and coccolithophores, and that both enantiomers are widespread in marine environments. A novel chiral-selective DHPS catabolic pathway was identified in marine Roseobacteraceae strains, where HpsO and HpsP dehydrogenases at the gateway to DHPS catabolism act specifically on R-DHPS and S-DHPS, respectively. R-DHPS is also a substrate for the dehydrogenase HpsN. All three dehydrogenases generate stable hydrogen bonds between the chirality-center hydroxyls of DHPS and highly conserved residues, and HpsP also form coordinate\u2013covalent bonds between the chirality-center hydroxyls and Zn2+, which determines the mechanistic basis of strict stereoselectivity. We further illustrated the role of enzymatic promiscuity in the evolution of DHPS metabolism in Roseobacteraceae and SAR11. This study provides the first evidence of chirality\u2019s involvement in phytoplankton-bacteria metabolic currencies, opening a new avenue for understanding the ocean organosulfur cycle.<\/jats:p>","DOI":"10.1093\/ismejo\/wrae084","type":"journal-article","created":{"date-parts":[[2024,5,6]],"date-time":"2024-05-06T18:18:41Z","timestamp":1715019521000},"source":"Crossref","is-referenced-by-count":9,"title":["Enantioselective transformation of phytoplankton-derived dihydroxypropanesulfonate by marine bacteria"],"prefix":"10.1093","volume":"18","author":[{"given":"Le","family":"Liu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiang","family":"Gao","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Cellular Stress Biology , Fujian Provincial Key Laboratory of Innovative Drug Target Research, School of Pharmaceutical Sciences, , Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Provincial Key Laboratory of Innovative Drug Target Research, School of Pharmaceutical Sciences, , Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Changjie","family":"Dong","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huanyu","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaofeng","family":"Chen","sequence":"additional","affiliation":[{"name":"Technical Innovation Center for Utilization of Marine Biological Resources, Third Institute of Oceanography, Ministry of Natural Resources , Xiamen 361001 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoyi","family":"Ma","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shujing","family":"Liu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Quanrui","family":"Chen","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dan","family":"Lin","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nianzhi","family":"Jiao","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kai","family":"Tang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Marine Environmental Science , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"},{"name":"Xiamen University , Fujian Key Laboratory of Marine Carbon Sequestration, College of Ocean and Earth Sciences, , Xiang'an South Road, Xiamen 361102 , China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2024,5,6]]},"reference":[{"key":"2024052814103185000_ref1","doi-asserted-by":"crossref","first-page":"26571","DOI":"10.1073\/pnas.1908241116","article-title":"On the possible origin of protein homochirality, structure, and biochemical function","volume":"116","author":"Skolnick","year":"2019","journal-title":"Proc Natl Acad Sci USA"},{"key":"2024052814103185000_ref2","doi-asserted-by":"crossref","first-page":"2324","DOI":"10.1021\/acs.accounts.8b00312","article-title":"Controlling supramolecular chirality in multicomponent self-assembled systems","volume":"51","author":"Xing","year":"2018","journal-title":"Acc Chem Res"},{"key":"2024052814103185000_ref3","doi-asserted-by":"crossref","first-page":"806","DOI":"10.1038\/s41570-022-00431-4","article-title":"Demystifying racemic natural products in the homochiral 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