{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:30:40Z","timestamp":1786977040257,"version":"build-2736575974"},"reference-count":67,"publisher":"Wiley","issue":"29","license":[{"start":{"date-parts":[[2025,5,22]],"date-time":"2025-05-22T00:00:00Z","timestamp":1747872000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["52233009"],"award-info":[{"award-number":["52233009"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["52350348"],"award-info":[{"award-number":["52350348"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["92356302"],"award-info":[{"award-number":["92356302"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["52021002"],"award-info":[{"award-number":["52021002"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["52425306"],"award-info":[{"award-number":["52425306"]}],"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":["2020YFA0710700"],"award-info":[{"award-number":["2020YFA0710700"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2025,7,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The selection of twenty canonical amino acids in protein synthesis is well\u2010established, yet the reasons behind their natural selection remain unclear. Specifically, why structurally similar analogs, such as\n                    <jats:italic>L<\/jats:italic>\n                    \u20102,4\u2010diaminobutyric acid (Dab) and\n                    <jats:italic>L<\/jats:italic>\n                    \u2010ornithine (Orn), are not chosen over\n                    <jats:italic>L<\/jats:italic>\n                    \u2010lysine (Lys) is unknown. These analogs differ only in alkyl chain length, raising the question of whether such variations influence polypeptide stability and natural selection. To investigate how unnatural amino acids affect the stability of synthesized polypeptides, we present the efficient synthesis of\n                    <jats:italic>o<\/jats:italic>\n                    \u2010nitrobenzyl (NB) carbamate\u2010caged photo\u2010responsive polypeptide amphiphiles based on Dab and Orn via polymerization of\n                    <jats:italic>N<\/jats:italic>\n                    \u2010phenoxycarbonyl\u2010functionalized amino acid precursors. Depending on the self\u2010assembly methods, these poly(ethylene glycol) (PEG)\u2010\n                    <jats:italic>b<\/jats:italic>\n                    \u2010polypeptide hybrid block copolymers formed various nanostructures, including two\u2010dimensional discs and oblate vesicles. Upon photoirradiation, the newly liberated primary amines underwent spontaneous cyclization with backbone amide linkages to generate thermodynamically stable 5\u2010 or 6\u2010membered lactams. Such a backbone degradation process eventually led to the disassembly and disintegration of the assemblies. These findings provide new insights into the natural selection of Lys, and open new possibilities for creating functional polypeptide\u2010based materials in drug delivery, tissue engineering, and other biomedical applications.\n                  <\/jats:p>","DOI":"10.1002\/anie.202502629","type":"journal-article","created":{"date-parts":[[2025,5,12]],"date-time":"2025-05-12T22:16:41Z","timestamp":1747088201000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Insight into Lysine Selection via Controlled Degradation of 2,4\u2010Diaminobutyric Acid and Ornithine Polypeptides"],"prefix":"10.1002","volume":"64","author":[{"given":"Mingxuan","family":"Hou","sequence":"first","affiliation":[{"name":"Department of Pharmacy The First Affiliated Hospital of University of Science and Technology of China (USTC) State Key Laboratory of Precision and Intelligent Chemistry Department of Polymer Science and Engineering University of Science and Technology of China  Hefei Anhui Province 230026 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenjin","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Pharmacy The First Affiliated Hospital of University of Science and Technology of China (USTC) State Key Laboratory of Precision and Intelligent Chemistry Department of Polymer Science and Engineering University of Science and Technology of China  Hefei Anhui Province 230026 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jie","family":"Cen","sequence":"additional","affiliation":[{"name":"Department of Pharmacy The First Affiliated Hospital of University of Science and Technology of China (USTC) State Key Laboratory of Precision and Intelligent Chemistry Department of Polymer Science and Engineering University of Science and Technology of China  Hefei Anhui Province 230026 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenhao","family":"Pan","sequence":"additional","affiliation":[{"name":"School of Chemistry and Materials Science University of Science and Technology of China  Hefei Anhui Province 230026 China"},{"name":"Suzhou Institute for Advanced Research University of Science and Technology of China  Suzhou Jiangsu Province 215123 China"},{"name":"School of Biomedical Engineering Division of Life Sciences and Medicine University of Science and Technology of China  Hefei Anhui Province 230026 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhengyu","family":"Deng","sequence":"additional","affiliation":[{"name":"School of Chemistry and Materials Science University of Science and Technology of China  Hefei Anhui Province 230026 China"},{"name":"Suzhou Institute for Advanced Research University of Science and Technology of China  Suzhou Jiangsu Province 215123 China"},{"name":"School of Biomedical Engineering Division of Life Sciences and Medicine University of Science and Technology of China  Hefei Anhui Province 230026 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinming","family":"Hu","sequence":"additional","affiliation":[{"name":"Department of Pharmacy The First Affiliated Hospital of University of Science and Technology of China (USTC) State Key Laboratory of Precision and Intelligent Chemistry Department of Polymer Science and Engineering University of Science and Technology of China  Hefei Anhui Province 230026 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9789-6282","authenticated-orcid":false,"given":"Shiyong","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Pharmacy The First Affiliated Hospital of University of Science and Technology of China (USTC) State Key Laboratory of Precision and Intelligent Chemistry Department of Polymer Science and Engineering University of Science and Technology of China  Hefei Anhui Province 230026 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,5,22]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600693"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2703"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.7b01569"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201902287"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00664"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-10792-y"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-022-00890-8"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b08801"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bpj.2018.10.031"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9032742"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00239-018-9876-2"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.3c00592"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35064e"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr2004844"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.202300492"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.2c00087"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1086501"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0405293101"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2315000121"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1007\/b136707"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1111\/febs.13982"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c12497"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01795749"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja068447g"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB00798J"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3py21094d"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/pola.26788"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.5b00455"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1904849116"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-16891-5"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(88)85099-8"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja307710d"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0403043101"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11084-008-9150-5"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1161527"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.3390\/life6010012"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2836(68)90392-6"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(73)90151-4"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1038\/381059a0"},{"key":"e_1_2_7_40_1","volume":"2021","author":"Li L.","year":"2021","journal-title":"Research"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00460E"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00297"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00712"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35115c"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.polymer.2020.122914"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS01114F"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/la035924p"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja409686x"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503551"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7PY01725A"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1006\/abio.1997.2366"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0431096"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-017-01372-z"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/ma021439"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00724a041"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0463738"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0009-2614(02)00784-4"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/marc.202100754"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202217365"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201916394"},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja984012k"},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja001033h"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00316a039"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmat1794"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC04053G"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biomaterials.2021.120913"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.progpolymsci.2021.101487"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202502629","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,29]],"date-time":"2025-11-29T18:18:11Z","timestamp":1764440291000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202502629"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,5,22]]},"references-count":67,"journal-issue":{"issue":"29","published-print":{"date-parts":[[2025,7,14]]}},"alternative-id":["10.1002\/anie.202502629"],"URL":"https:\/\/doi.org\/10.1002\/anie.202502629","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,5,22]]},"assertion":[{"value":"2025-01-31","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-12","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-22","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202502629"}}