{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,27]],"date-time":"2025-05-27T09:33:56Z","timestamp":1748338436653,"version":"3.37.3"},"reference-count":47,"publisher":"Springer Science and Business Media LLC","issue":"5","license":[{"start":{"date-parts":[[2022,10,19]],"date-time":"2022-10-19T00:00:00Z","timestamp":1666137600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2022,10,19]],"date-time":"2022-10-19T00:00:00Z","timestamp":1666137600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/100012352","name":"Universit\u00e0 degli Studi di Milano","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100012352","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Mol Divers"],"published-print":{"date-parts":[[2023,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Various boron-containing isocyanides have been efficiently synthesized from the corresponding enantiopure \u03b2-substituted \u03b2-amino boronic acid pinacol esters, without need for protecting group interconversion, through a two-step, purification-free procedure. They were employed in a variety of isocyanide-based multicomponent reactions, proving to be reliable components for all of them and allowing the efficient synthesis of unprecedented, boron-containing peptidomimetics and heteroatom-rich small molecules, including biologically relevant cyclic boronates. Jointing together the \u03b2-amido boronic acid moiety, deriving from the isocyanide component, with prominent pharmacophoric rings emerging from the multicomponent process, a successful application of the molecular hybridization concept could be realized.<\/jats:p>\n                <jats:p><jats:bold>Graphical abstract<\/jats:bold><\/jats:p>","DOI":"10.1007\/s11030-022-10549-8","type":"journal-article","created":{"date-parts":[[2022,10,19]],"date-time":"2022-10-19T02:03:31Z","timestamp":1666145011000},"page":"2161-2168","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Enantiopure \u03b2-isocyano-boronic esters: synthesis and exploitation in isocyanide-based multicomponent reactions"],"prefix":"10.1007","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8829-0772","authenticated-orcid":false,"given":"Marco","family":"Manenti","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Simone","family":"Gusmini","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Leonardo","family":"Lo Presti","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Giorgio","family":"Molteni","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0397-2636","authenticated-orcid":false,"given":"Alessandra","family":"Silvani","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2022,10,19]]},"reference":[{"key":"10549_CR1","volume-title":"Isocyanide chemistry applications in synthesis and materials science","author":"V Nenajdenko","year":"2012","unstructured":"Nenajdenko V (2012) Isocyanide chemistry applications in synthesis and materials science. Wiley, Weinheim"},{"key":"10549_CR2","doi-asserted-by":"publisher","first-page":"53203","DOI":"10.1039\/C6RA02143C","volume":"6","author":"S Sadjadi","year":"2016","unstructured":"Sadjadi S, Heravi MM, Nazari N (2016) Isocyanide-based multicomponent reactions in the synthesis of heterocycles. RSC Adv 6:53203\u201353272. https:\/\/doi.org\/10.1039\/C6RA02143C","journal-title":"RSC Adv"},{"key":"10549_CR3","doi-asserted-by":"publisher","first-page":"9160","DOI":"10.3390\/ijms21239160","volume":"21","author":"N Cankarov\u00e1","year":"2020","unstructured":"Cankarov\u00e1 N, Krchn\u00e1k V (2020) Isocyanide multicomponent reactions on solid phase: state of the art and future application. Int J Mol Sci 21:9160. https:\/\/doi.org\/10.3390\/ijms21239160","journal-title":"Int J Mol Sci"},{"key":"10549_CR4","doi-asserted-by":"publisher","first-page":"9298","DOI":"10.1039\/d1nj05994g","volume":"46","author":"SG Pharande","year":"2022","unstructured":"Pharande SG, Renter\u00eca-G\u00f2mez MA, G\u00e1mez-Monta\u00f1o R (2022) Mechanochemical IMCR and IMCR-post transformation domino strategies: towards the sustainable DOS of dipeptide-like and heterocyclic peptidomimetics. New J Chem 46:9298. https:\/\/doi.org\/10.1039\/d1nj05994g","journal-title":"New J Chem"},{"key":"10549_CR5","doi-asserted-by":"publisher","first-page":"6598","DOI":"10.1002\/chem.202003224","volume":"27","author":"J Luo","year":"2021","unstructured":"Luo J, Chen G-S, Chen S-J, Li Z-D, Liu Y-L (2021) Catalytic enantioselective isocyanide-based reactions: beyond passerini and Ugi multicomponent reactions. Chem Eur J 27:6598\u20136619. https:\/\/doi.org\/10.1002\/chem.202003224","journal-title":"Chem Eur J"},{"key":"10549_CR6","doi-asserted-by":"publisher","first-page":"7238","DOI":"10.1021\/acs.orglett.9b02448","volume":"21","author":"VBK Kunig","year":"2019","unstructured":"Kunig VBK, Ehrt C, D\u00f6mling A, Brunschweiger A (2019) Isocyanide multicomponent reactions on solid-phase-coupled DNA oligonucleotides for encoded library synthesis. Org Lett 21:7238\u20137243. https:\/\/doi.org\/10.1021\/acs.orglett.9b02448","journal-title":"Org Lett"},{"issue":"4","key":"10549_CR7","doi-asserted-by":"publisher","first-page":"345","DOI":"10.2174\/1386207323666200219124625","volume":"23","author":"AH Najar","year":"2020","unstructured":"Najar AH, Hossaini Z, Abdolmohammadi S, Zareyee D (2020) ZnO-nanorods promoted synthesis of \u03b1-amino nitrile benzofuran derivatives using one-pot multicomponent reaction of isocyanides. Comb Chem High Throughput Screen 23(4):345\u2013355. https:\/\/doi.org\/10.2174\/1386207323666200219124625","journal-title":"Comb Chem High Throughput Screen"},{"key":"10549_CR8","doi-asserted-by":"publisher","first-page":"544","DOI":"10.3762\/bjoc.10.50","volume":"10","author":"G Koopmanschap","year":"2014","unstructured":"Koopmanschap G, Ruijter E, Orru RVA (2014) Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics. Beilstein J Org Chem 10:544\u2013598. https:\/\/doi.org\/10.3762\/bjoc.10.50","journal-title":"Beilstein J Org Chem"},{"key":"10549_CR9","doi-asserted-by":"publisher","first-page":"4","DOI":"10.3390\/ecsoc-24-08396","volume":"3","author":"SC Ram\u00edrez-L\u00f3pez","year":"2021","unstructured":"Ram\u00edrez-L\u00f3pez SC, Renter\u00eda-G\u00f3mez MA, Alvarado CRS, G\u00e1mez-Monta\u00f1o R (2021) Synthesis of peptidomimetics via IMCR\/post-transformation strategy. Chem Proc 3:4. https:\/\/doi.org\/10.3390\/ecsoc-24-08396","journal-title":"Chem Proc"},{"key":"10549_CR10","doi-asserted-by":"publisher","first-page":"42644","DOI":"10.1039\/d0ra07501a","volume":"10","author":"MA Fouad","year":"2020","unstructured":"Fouad MA, Abdel-Hamid H, Ayoup MS (2020) Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications. RSC Adv 10:42644\u201342681. https:\/\/doi.org\/10.1039\/d0ra07501a","journal-title":"RSC Adv"},{"key":"10549_CR11","doi-asserted-by":"publisher","first-page":"332","DOI":"10.1002\/slct.202004131","volume":"6","author":"SG Pharande","year":"2021","unstructured":"Pharande SG (2021) The merger of isocyanide-based multicomponent reaction and ring-closing metathesis (IMCR\/RCM). ChemistrySelect 6:332\u2013346. https:\/\/doi.org\/10.1002\/slct.202004131","journal-title":"ChemistrySelect"},{"key":"10549_CR12","doi-asserted-by":"publisher","first-page":"153353","DOI":"10.1016\/j.tetlet.2021.153353","volume":"81","author":"KM Pandya","year":"2021","unstructured":"Pandya KM, Battula S, Naik PJ (2021) Pd-catalyzed post-Ugi intramolecular cyclization to the synthesis of isoquinolone-pyrazole hybrid pharmacophores & discover their antimicrobial and DFT studies. Tetrahedron Lett 81:153353. https:\/\/doi.org\/10.1016\/j.tetlet.2021.153353","journal-title":"Tetrahedron Lett"},{"issue":"6","key":"10549_CR13","doi-asserted-by":"publisher","first-page":"3083","DOI":"10.1021\/cr100233r","volume":"112","author":"A D\u00f6mling","year":"2012","unstructured":"D\u00f6mling A, Wang W, Wang K (2012) Chemistry and biology of multicomponent reactions. Chem Rev 112(6):3083\u20133135. https:\/\/doi.org\/10.1021\/cr100233r","journal-title":"Chem Rev"},{"key":"10549_CR14","doi-asserted-by":"publisher","first-page":"687","DOI":"10.1039\/c9ob02249j","volume":"18","author":"S Hosokawa","year":"2020","unstructured":"Hosokawa S, Nakanishi K, Udagawa Y, Maeda M, Sato S, Nakano K, Masuda T, Ichikawa Y (2020) Total synthesis of exigurin: the Ugi reaction in a hypothetical biosynthesis of natural products. Org Biomol Chem 18:687. https:\/\/doi.org\/10.1039\/c9ob02249j","journal-title":"Org Biomol Chem"},{"key":"10549_CR15","doi-asserted-by":"publisher","first-page":"1790","DOI":"10.1021\/ja1113003","volume":"133","author":"O Kreye","year":"2011","unstructured":"Kreye O, Toth T, Meier MAR (2011) Introducing multicomponent reactions to polymer science: Passerini reactions of renewable monomers. J Am Chem Soc 133:1790\u20131792. https:\/\/doi.org\/10.1021\/ja1113003","journal-title":"J Am Chem Soc"},{"key":"10549_CR16","doi-asserted-by":"publisher","first-page":"34903","DOI":"10.1039\/c8ra08165d","volume":"8","author":"G Rainoldi","year":"2018","unstructured":"Rainoldi G, Lesma G, Picozzi C, Lo Presti L, Silvani A (2018) One step access to oxindole-based \u03b2-lactams through Ugi four-center three-component reaction. RSC Adv 8:34903\u201334910. https:\/\/doi.org\/10.1039\/c8ra08165d","journal-title":"RSC Adv"},{"key":"10549_CR17","doi-asserted-by":"publisher","first-page":"98","DOI":"10.1021\/acscombsci.7b00179","volume":"20","author":"G Rainoldi","year":"2018","unstructured":"Rainoldi G, Begnini F, De Munnik M, Lo Presti L, Vande Velde CML, Orru R, Lesma G, Ruijter E, Silvani A (2018) Sequential multicomponent strategy for the diastereoselective synthesis of densely functionalized spirooxindole-fused thiazolidines. ACS Comb Sci 20:98\u2013105. https:\/\/doi.org\/10.1021\/acscombsci.7b00179","journal-title":"ACS Comb Sci"},{"key":"10549_CR18","doi-asserted-by":"publisher","first-page":"3907","DOI":"10.1055\/s-0035-1562497","volume":"48","author":"G Lesma","year":"2016","unstructured":"Lesma G, Luraghi A, Rainoldi G, Mattiuzzo E, Bortolozzi R, Viola G, Silvani A (2016) Multicomponent approach to bioactive peptide-ecdysteroid conjugates: creating diversity at C6 by means of the Ugi reaction. Synthesis 48:3907\u20133916. https:\/\/doi.org\/10.1055\/s-0035-1562497","journal-title":"Synthesis"},{"key":"10549_CR19","doi-asserted-by":"publisher","first-page":"11633","DOI":"10.1039\/c5ob01882j","volume":"13","author":"G Lesma","year":"2015","unstructured":"Lesma G, Bassanini I, Bortolozzi R, Colletto C, Bai R, Hamel E, Meneghetti F, Rainoldi G, Stucchi M, Sacchetti A, Silvani A, Viola G (2015) Complementary isonitrile-based multicomponent reactions for the synthesis of diversified cytotoxic hemiasterlin analogues. Org Biomol Chem 13:11633\u201311644. https:\/\/doi.org\/10.1039\/c5ob01882j","journal-title":"Org Biomol Chem"},{"key":"10549_CR20","doi-asserted-by":"publisher","first-page":"882","DOI":"10.1021\/acsmedchemlett.5b00131","volume":"6","author":"M Stucchi","year":"2015","unstructured":"Stucchi M, Gmeiner P, Huebner H, Rainoldi G, Sacchetti A, Silvani A, Lesma G (2015) Multicomponent synthesis and biological evaluation of a piperazine-based dopamine receptor ligand library. ACS Med Chem Lett 6:882\u2013887. https:\/\/doi.org\/10.1021\/acsmedchemlett.5b00131","journal-title":"ACS Med Chem Lett"},{"key":"10549_CR21","doi-asserted-by":"publisher","first-page":"4993","DOI":"10.1039\/c5ob00218d","volume":"13","author":"M Stucchi","year":"2015","unstructured":"Stucchi M, Cairati S, Cetin-Atalay R, Christodoulou MS, Grazioso G, Pescitelli G, Silvani A, Yildirim DC, Lesma G (2015) Application of the Ugi reaction with multiple amino acid-derived components: synthesis and conformational evaluation of piperazine-based minimalist peptidomimetics. Org Biomol Chem 13:4993\u20135005. https:\/\/doi.org\/10.1039\/c5ob00218d","journal-title":"Org Biomol Chem"},{"key":"10549_CR22","doi-asserted-by":"publisher","first-page":"1383","DOI":"10.3762\/bjoc.10.141","volume":"10","author":"G Lesma","year":"2014","unstructured":"Lesma G, Meneghetti F, Sacchetti A, Stucchi M, Silvani A (2014) Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives. Beilstein J Org Chem 10:1383\u20131389. https:\/\/doi.org\/10.3762\/bjoc.10.141","journal-title":"Beilstein J Org Chem"},{"key":"10549_CR23","doi-asserted-by":"publisher","first-page":"3994","DOI":"10.1016\/j.tet.2014.04.081","volume":"70","author":"A Silvani","year":"2014","unstructured":"Silvani A, Lesma G, Crippa S, Vece V (2014) Multicomponent access to novel dihydroimidazo [10,50:1,2]pyrido[3,4-b]indol-2-ium salts and indoles by means of Ugi\/Bischler-Napieralski\/heterocyclization two step strategy. Tetrahedron 70:3994\u20134001. https:\/\/doi.org\/10.1016\/j.tet.2014.04.081","journal-title":"Tetrahedron"},{"key":"10549_CR24","doi-asserted-by":"publisher","first-page":"9004","DOI":"10.1039\/c2ob26301g","volume":"10","author":"G Lesma","year":"2012","unstructured":"Lesma G, Cecchi R, Crippa S, Giovanelli P, Meneghetti F, Musolino M, Sacchetti A, Silvani A (2012) Ugi 4-CR\/pictet-spengler reaction as a short route to tryptophan-derived peptidomimetics. Org Biomol Chem 10:9004\u20139012. https:\/\/doi.org\/10.1039\/c2ob26301g","journal-title":"Org Biomol Chem"},{"key":"10549_CR25","doi-asserted-by":"publisher","first-page":"7211","DOI":"10.1039\/d1ob01303c","volume":"19","author":"M Manenti","year":"2021","unstructured":"Manenti M, Gazzotti S, Lo Presti L, Molteni G, Silvani A (2021) Highly diastereoselective entry to chiral oxindole-based \u03b2-amino boronic acids and spiro derivatives. Org Biomol Chem 19:7211\u20137216. https:\/\/doi.org\/10.1039\/d1ob01303c","journal-title":"Org Biomol Chem"},{"key":"10549_CR26","doi-asserted-by":"publisher","first-page":"1","DOI":"10.3390\/antibiotics9050249","volume":"249","author":"E Bassini","year":"2020","unstructured":"Bassini E, Gazzotti S, Sannio F, Grazioso G, Silvani A (2020) Isonitrile-based multicomponent synthesis of \u03b2-amino boronic acids as \u03b2-lactamase inhibitors. Antibiotics 249:1\u201321. https:\/\/doi.org\/10.3390\/antibiotics9050249","journal-title":"Antibiotics"},{"key":"10549_CR27","doi-asserted-by":"publisher","first-page":"7296","DOI":"10.1021\/acs.joc.8b00325","volume":"83","author":"SJ Kaldas","year":"2018","unstructured":"Kaldas SJ, Rogova T, Nenajdenko VG, Yudin AK (2018) Modular synthesis of \u03b2-amino boronate peptidomimetics. J Org Chem 83:7296\u20137302. https:\/\/doi.org\/10.1021\/acs.joc.8b00325","journal-title":"J Org Chem"},{"key":"10549_CR28","doi-asserted-by":"publisher","first-page":"5033","DOI":"10.1039\/d2cc00659f","volume":"58","author":"V Trudel","year":"2022","unstructured":"Trudel V, Brien C, Tana J, Yudin AK (2022) Towards depeptidized aminoboronic acid derivatives through the use of borylated iminium ions. Chem Commun 58:5033\u20135036. https:\/\/doi.org\/10.1039\/d2cc00659f","journal-title":"Chem Commun"},{"key":"10549_CR29","doi-asserted-by":"publisher","first-page":"e202200435","DOI":"10.1002\/ejoc.202200435","volume":"25","author":"M Manenti","year":"2022","unstructured":"Manenti M, Gusmini S, Lo Presti L, Silvani A (2022) Exploiting enantiopure \u03b2-amino boronic acids in isocyanide-based multicomponent reactions. Eur J Org Chem 25:e202200435. https:\/\/doi.org\/10.1002\/ejoc.202200435","journal-title":"Eur J Org Chem"},{"key":"10549_CR30","doi-asserted-by":"publisher","first-page":"1760","DOI":"10.1038\/s41467-017-01319-4","volume":"8","author":"J Tan","year":"2017","unstructured":"Tan J, Cognetta AB, Diaz DB, Lum KM, Adachi S, Kundu S, Cravatt BF, Yudin AK (2017) Multicomponent mapping of boron chemotypes furnishes selective enzyme inhibitors. Nat Commun 8:1760. https:\/\/doi.org\/10.1038\/s41467-017-01319-4","journal-title":"Nat Commun"},{"key":"10549_CR31","doi-asserted-by":"publisher","first-page":"17706","DOI":"10.1021\/acs.jmedchem.1c01691","volume":"64","author":"YC Xiao","year":"2021","unstructured":"Xiao YC, Yu JL, DaiQ-Q LG, Li G-B (2021) Targeting metalloenzymes by boron-containing metal-binding pharmacophores. J Med Chem 64:17706\u201317727. https:\/\/doi.org\/10.1021\/acs.jmedchem.1c01691","journal-title":"J Med Chem"},{"key":"10549_CR32","doi-asserted-by":"publisher","first-page":"2109","DOI":"10.1016\/0040-4039(95)00168-c","volume":"36","author":"J Versleijen","year":"1995","unstructured":"Versleijen J, Faber P, Bodewes H, Braker A, Van Leusen D, Van Leusen A (1995) On the synthesis of boron substituted methyl isocyanides: 2-isocyanomethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. Tetrahedron Lett 36:2109. https:\/\/doi.org\/10.1016\/0040-4039(95)00168-c","journal-title":"Tetrahedron Lett"},{"key":"10549_CR33","doi-asserted-by":"publisher","first-page":"8411","DOI":"10.1002\/anie.201302818","volume":"52","author":"A Zajdlik","year":"2013","unstructured":"Zajdlik A, Wang Z, Hickey JL, Aman A, Schimmer AD, Yudin AK (2013) \u03b1-boryl isocyanidesenable facile preparation of bioactive boropeptides. Angew Chem Int Ed 52:8411\u20138415. https:\/\/doi.org\/10.1002\/anie.201302818","journal-title":"Angew Chem Int Ed"},{"key":"10549_CR34","doi-asserted-by":"publisher","first-page":"9926","DOI":"10.1021\/ja304173d","volume":"134","author":"Z He","year":"2012","unstructured":"He Z, Zajdlik A, St. Denis JD, Assem N, Yudin AK (2012) Boroalkyl group migration provides a versatile entry into \u03b1-aminoboronic acid derivatives. J Am Chem Soc 134:9926\u20139929. https:\/\/doi.org\/10.1021\/ja304173d","journal-title":"J Am Chem Soc"},{"key":"10549_CR35","doi-asserted-by":"publisher","first-page":"6377","DOI":"10.1021\/acs.jmedchem.9b00878","volume":"62","author":"J Tan","year":"2019","unstructured":"Tan J, Grouleff JJ, Jitkova Y, Diaz DB, Griffith EC, Shao W, Yudin AK et al (2019) De novo design of boron-based peptidomimetics as potent inhibitors of human ClpP in the presence of human ClpX. J Med Chem 62:6377\u20136390. https:\/\/doi.org\/10.1021\/acs.jmedchem.9b00878","journal-title":"J Med Chem"},{"key":"10549_CR36","doi-asserted-by":"publisher","first-page":"6687","DOI":"10.1039\/d1ob00616a","volume":"19","author":"F Fini","year":"2021","unstructured":"Fini F, Zanni A, Introvigne ML, Stucchi M, Caselli E, Prati F (2021) Straightforward synthesis of chiral non-racemic \u03b1-boryl isocyanides. Org Biomol Chem 19:6687\u20136691. https:\/\/doi.org\/10.1039\/d1ob00616a","journal-title":"Org Biomol Chem"},{"key":"10549_CR37","doi-asserted-by":"publisher","first-page":"1210","DOI":"10.1021\/acs.orglett.6b00376","volume":"18","author":"J Park","year":"2016","unstructured":"Park J, Lee Y, Kim J, Cho SH (2016) Copper-catalyzed diastereoselective addition of diborylmethane to N-tert-butanesulfinyl aldimines: synthesis of \u03b2-aminoboronates. Org Lett 18:1210. https:\/\/doi.org\/10.1021\/acs.orglett.6b00376","journal-title":"Org Lett"},{"key":"10549_CR38","doi-asserted-by":"publisher","first-page":"1694","DOI":"10.2174\/1568026619666190619115735","volume":"19","author":"V Ivasiv","year":"2019","unstructured":"Ivasiv V, Albertini C, Gon\u00e7alves AE, Rossi M, Bolognesi ML (2019) Molecular hybridization as a tool for designing multitarget drug candidates for complex deseases. Curr Topics Med Chem 19:1694\u20131711. https:\/\/doi.org\/10.2174\/1568026619666190619115735","journal-title":"Curr Topics Med Chem"},{"key":"10549_CR39","doi-asserted-by":"publisher","first-page":"1829","DOI":"10.2174\/092986707781058805","volume":"14","author":"C Viegas-Junior","year":"2007","unstructured":"Viegas-Junior C, Danuello A, Da Silva BA, Barreiro EJ, Fraga CAM (2007) Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem 14:1829\u20131852. https:\/\/doi.org\/10.2174\/092986707781058805","journal-title":"Curr Med Chem"},{"key":"10549_CR40","doi-asserted-by":"publisher","first-page":"2211","DOI":"10.1016\/j.tetlet.2012.02.078","volume":"53","author":"AT Khan","year":"2012","unstructured":"Khan AT, Basha RS, Lal M (2012) Bromodimethylsulfonium bromide (BDMS) catalyzed synthesis of imidazo[1,2-a] pyridine derivatives and their fluorescence properties. Tetrahedron Lett 53:2211\u20132217. https:\/\/doi.org\/10.1016\/j.tetlet.2012.02.078","journal-title":"Tetrahedron Lett"},{"key":"10549_CR41","doi-asserted-by":"publisher","first-page":"840","DOI":"10.3390\/antibiotics11070840","volume":"11","author":"GM Tuveri","year":"2022","unstructured":"Tuveri GM, Ceccarelli M, Pira A, Bodrenko IV (2022) The optimal permeation of cyclic boronates to cross the outer membrane via the porin pathway. Antibiotics 11:840. https:\/\/doi.org\/10.3390\/antibiotics11070840","journal-title":"Antibiotics"},{"key":"10549_CR42","doi-asserted-by":"publisher","first-page":"491","DOI":"10.1039\/c9md00557a","volume":"11","author":"CL Tooke","year":"2020","unstructured":"Tooke CL, Hinchliffe P, Krajnc A, Mulholland AJ, Brem J, Schofield CJ, Spencer J (2020) Cyclic boronates as versatile scaffolds for KPC-2 \u03b2-lactamase inhibition. RSC Med Chem 11:491\u2013496. https:\/\/doi.org\/10.1039\/c9md00557a","journal-title":"RSC Med Chem"},{"key":"10549_CR43","doi-asserted-by":"publisher","first-page":"1398","DOI":"10.1021\/acsinfecdis.9b00330","volume":"6","author":"A Parkova","year":"2020","unstructured":"Parkova A, Lucic A, Krajnc A, Brem J, Calvopi\u00f1a K, Langley GW, McDonough MA, Trapencieris P, Schofield CJ (2020) Broad spectrum \u03b2-lactamase inhibition by a thioether substituted bicyclic boronate. ACS Infect Dis 6:1398\u20131404. https:\/\/doi.org\/10.1021\/acsinfecdis.9b00330","journal-title":"ACS Infect Dis"},{"key":"10549_CR44","doi-asserted-by":"publisher","first-page":"2835","DOI":"10.1021\/ja312532x","volume":"135","author":"JS Laursen","year":"2013","unstructured":"Laursen JS, Engel-Andreasen J, Fristrup P, Harris P, Olsen CA (2013) Cis-trans amide bond rotamers in \u03b2-peptoids and peptoids: evaluation of stereoelectronic effects in backbone and side chains. J Am Chem Soc 135:2835\u20132844. https:\/\/doi.org\/10.1021\/ja312532x","journal-title":"J Am Chem Soc"},{"key":"10549_CR45","unstructured":"CCDC 2192101 contains the supplementary crystallographic data. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk\/structures"},{"key":"10549_CR46","doi-asserted-by":"publisher","first-page":"2215","DOI":"10.1039\/c2ay25346a","volume":"4","author":"K Lawrence","year":"2012","unstructured":"Lawrence K, Flower SE, Kociok-Kohn G, Frost CG, James TD (2012) A simple and effective colorimetric technique for the detection of boronic acids and their derivatives. Anal Methods 4:2215. https:\/\/doi.org\/10.1039\/c2ay25346a","journal-title":"Anal Methods"},{"key":"10549_CR47","doi-asserted-by":"publisher","first-page":"3048","DOI":"10.1021\/acs.orglett.9b00584","volume":"21","author":"P Stefan","year":"2019","unstructured":"Stefan P, Hinkes A, Klein CDP (2019) Virtues of volatility: a facile transesterification approach to boronic acids. Org Lett 21:3048. https:\/\/doi.org\/10.1021\/acs.orglett.9b00584","journal-title":"Org Lett"}],"container-title":["Molecular Diversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s11030-022-10549-8.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1007\/s11030-022-10549-8\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s11030-022-10549-8.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,25]],"date-time":"2023-09-25T12:38:24Z","timestamp":1695645504000},"score":1,"resource":{"primary":{"URL":"https:\/\/link.springer.com\/10.1007\/s11030-022-10549-8"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,10,19]]},"references-count":47,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2023,10]]}},"alternative-id":["10549"],"URL":"https:\/\/doi.org\/10.1007\/s11030-022-10549-8","relation":{},"ISSN":["1381-1991","1573-501X"],"issn-type":[{"type":"print","value":"1381-1991"},{"type":"electronic","value":"1573-501X"}],"subject":[],"published":{"date-parts":[[2022,10,19]]},"assertion":[{"value":"29 July 2022","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"7 October 2022","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"19 October 2022","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}}]}}