{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,5]],"date-time":"2026-03-05T16:35:12Z","timestamp":1772728512469,"version":"3.50.1"},"reference-count":49,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2023,1,31]],"date-time":"2023-01-31T00:00:00Z","timestamp":1675123200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004731","name":"Natural Science Foundation of Zhejiang Province","doi-asserted-by":"publisher","award":["LQ22B020001"],"award-info":[{"award-number":["LQ22B020001"]}],"id":[{"id":"10.13039\/501100004731","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004731","name":"Natural Science Foundation of Zhejiang Province","doi-asserted-by":"publisher","award":["22101260"],"award-info":[{"award-number":["22101260"]}],"id":[{"id":"10.13039\/501100004731","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["LQ22B020001"],"award-info":[{"award-number":["LQ22B020001"]}],"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":["22101260"],"award-info":[{"award-number":["22101260"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Traditional macrocyclic molecules encode recognition sites in their structural backbones, which limits the variation of the recognition sites and thus, would restrict the adjustment of recognition properties. Here, we report a new oligoamide-based macrocycle capable of varying the recognition functional groups by post-synthesis modification on its structural backbone. Through six steps of common reactions, the parent macrocycle (9) can be produced in gram scale with an overall yield of 31%. The post-synthesis modification of 9 to vary the recognition sites are demonstrated by producing four different macrocycles (10\u201313) with distinct functional groups, 2-methoxyethoxyl (10), hydroxyl (11), carboxyl (12) and amide (13), respectively. The 1H NMR study suggests that the structure of these macrocycles is consistent with our design, i.e., forming hydrogen bonding network at both rims of the macrocyclic backbone. The 1H-1H NOESY NMR study indicates the recognition functional groups are located inside the cavity of macrocycles. At last, a preliminary molecular recognition study shows 10 can recognize n-octyl-\u03b2-D-glucopyranoside (14) in chloroform.<\/jats:p>","DOI":"10.3390\/molecules28031338","type":"journal-article","created":{"date-parts":[[2023,2,1]],"date-time":"2023-02-01T01:36:59Z","timestamp":1675215419000},"page":"1338","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Recognition Site Modifiable Macrocycle: Synthesis, Functional Group Variation and Structural Inspection"],"prefix":"10.3390","volume":"28","author":[{"given":"Linmeng","family":"Fan","sequence":"first","affiliation":[{"name":"Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Life Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Min","family":"Du","sequence":"additional","affiliation":[{"name":"Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Life Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lichun","family":"Kong","sequence":"additional","affiliation":[{"name":"Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Life Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yan","family":"Cai","sequence":"additional","affiliation":[{"name":"Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Life Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiaobo","family":"Hu","sequence":"additional","affiliation":[{"name":"Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Life Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,31]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1293","DOI":"10.1351\/pac198961071293","article-title":"Protein-carbohydrate interactions: Basic molecular features","volume":"61","author":"Quiocho","year":"1989","journal-title":"Pure Appl. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1016\/S0959-440X(94)90170-8","article-title":"Structure and energetic of protein-carbohydrate complexes","volume":"4","author":"Toone","year":"1994","journal-title":"Curr. Opin. Struct. Biol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"27059","DOI":"10.1074\/jbc.M302642200","article-title":"Crystal Structure of Fungal Lectin six-bladed \u03b2-propeller fold and novel fucose recognition mode for aleuria aurantia lectin","volume":"278","author":"Wimmerova","year":"2003","journal-title":"J. Biol. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1124\/pr.107.07110","article-title":"Sortase as a Target of Anti-Infective Therapy","volume":"60","author":"Maresso","year":"2008","journal-title":"Pharmacol. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1002\/bip.21472","article-title":"Sortase transpeptidases: Insights into mechanism, substrate specificity, and inhibition","volume":"94","author":"Clancy","year":"2010","journal-title":"Peptide Sci."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1146\/annurev-cellbio-100617-062527","article-title":"Sortase A: A Model for Transpeptidation and Its Biological Applications","volume":"34","author":"Pishesha","year":"2018","journal-title":"Annu. Rev. Cell Dev. Biol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1021\/ar960298r","article-title":"Foldamers: A manifesto","volume":"31","author":"Gellman","year":"1998","journal-title":"Acc. Chem. Res."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5271","DOI":"10.1021\/cr300116k","article-title":"Aromatic Amide Foldamers: Structures, Properties, and Functions","volume":"112","author":"Zhang","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1038\/nchem.1568","article-title":"Inhibition of \u03b1-helix-mediated protein\u2013protein interactions using designed molecules","volume":"5","author":"Azzarito","year":"2013","journal-title":"Nat. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"334","DOI":"10.1038\/nchem.2195","article-title":"Iterative design of a helically folded aromatic oligoamide sequence for the selective encapsulation of fructose","volume":"7","author":"Chandramouli","year":"2015","journal-title":"Nat. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1137","DOI":"10.1021\/acs.joc.5b02671","article-title":"Solid-Phase Synthesis of Water-Soluble Helically Folded Hybrid \u03b1-Amino Acid\/Quinoline Oligoamides","volume":"81","author":"Hu","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"14239","DOI":"10.1021\/jacs.9b06094","article-title":"Folding and Assembly of Short \u03b1, \u03b2, \u03b3-Hybrid Peptides: Minor Variations in Sequence and Drastic Differences in Higher-Level Structures","volume":"141","author":"Zhang","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"11663","DOI":"10.1002\/chem.202101221","article-title":"A Disulfide Switch Providing Absolute Handedness Control in Double Helices via Conversion from the Antiparallel to Parallel Helical Pattern","volume":"27","author":"Li","year":"2021","journal-title":"Chem. Eur. J."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"e202108364","DOI":"10.1002\/anie.202108364","article-title":"Conformational Adaptation of b-Peptide Foldamers for the Formation of Metal\u2013Peptide Frameworks","volume":"61","author":"Jeong","year":"2022","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"15988","DOI":"10.1021\/jacs.2c05234","article-title":"Adaptive Binding of Alkyl Glycosides by Nonpeptidic Helix Bundles in Water: Toward Artificial Glycolipid Binding Proteins","volume":"144","author":"Yoo","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2723","DOI":"10.1021\/cr020080k","article-title":"Crown Ethers: Sensors for Ions and Molecular Scaffolds for Materials andBiological Models","volume":"104","author":"Gokel","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4844","DOI":"10.1002\/anie.200460675","article-title":"The Cucurbit[n]uril Family","volume":"44","author":"Lagona","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"704","DOI":"10.1038\/nchem.1668","article-title":"A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes","volume":"5","author":"Lee","year":"2013","journal-title":"Nat. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Basilotta, R., Mannino, D., Filippone, A., Casili, G., Prestifilippo, A., Colarossi, L., Raciti, G., Esposito, E., and Campolo, M. (2021). Role of Calixarene in Chemotherapy Delivery Strategies. Molecules, 26.","DOI":"10.3390\/molecules26133963"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Lebr\u00f3n, A.J., L\u00f3pez-L\u00f3pez, M., Garc\u00eda-Calder\u00f3n, B.C., Rosado, V.I., Balestra, R.F., Huertas, P., Rodik, V.R., Kalchenko, I.V., Bernal, E., and Moy\u00e1, L.M. (2021). Multivalent Calixarene-Based Liposomes as Platforms for Gene and Drug Delivery. Pharmaceutics, 13.","DOI":"10.3390\/pharmaceutics13081250"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3191","DOI":"10.1021\/acs.accounts.2c00555","article-title":"Pillararene-Inspired Macrocycles: From Extended Pillar[n]arenes to Geminiarenes","volume":"55","author":"Wu","year":"2022","journal-title":"Acc. Chem. Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"e202211387","DOI":"10.1002\/anie.202211387","article-title":"The Story of the Little Blue Box: A Tribute to Siegfried H\u00fcnig","volume":"62","author":"Chen","year":"2023","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1039\/C4CS00222A","article-title":"Metal\u2013organic molecular cages: Applications of biochemical implications","volume":"44","author":"Ahmad","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1770","DOI":"10.1021\/ja5120437","article-title":"Cooperative Loading and Release Behavior of a Metal\u2212Organic Receptor","volume":"137","author":"Gan","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2531","DOI":"10.1039\/C9CS00391F","article-title":"Biomimetic carbohydrate recognition","volume":"49","author":"Davis","year":"2020","journal-title":"Chem. Soc. Rev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"9527","DOI":"10.1039\/D1OB01737C","article-title":"Molecular cages for biological applications","volume":"19","author":"Tapia","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"13636","DOI":"10.1021\/acs.chemrev.2c00198","article-title":"Purely Covalent Molecular Cages and Containers for Guest Encapsulation","volume":"122","year":"2022","journal-title":"Chem. Rev."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2947","DOI":"10.1002\/1521-3773(20020816)41:16<2947::AID-ANIE2947>3.0.CO;2-H","article-title":"Molecular Recognition of Carbohydrates through Directional Hydrogen Bonds by Urea-Appended Porphyrins in Organic Media","volume":"41","author":"Kim","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4377","DOI":"10.1021\/ja068754m","article-title":"Pyrrolic Tripodal Receptors Effectively Recognizing Monosaccharides. Affinity Assessment through a Generalized Binding Descriptor","volume":"129","author":"Nativi","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1742","DOI":"10.1016\/j.ccr.2012.02.001","article-title":"Inorganic and organometallic hemicagepodates and cage cryptates incorporating a benzene platform","volume":"256","author":"Denis","year":"2012","journal-title":"Coordin. Chem. Rev."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"16040","DOI":"10.1039\/C8NJ02217H","article-title":"Comparative studies of the electronic, bindingand photophysical properties of a new nona-dentate hemi-cage tripodal HQ pendanttrizaza-macrocycle with unfilled, half-filled and completely filled lanthanide ions","volume":"42","author":"Rohini","year":"2018","journal-title":"New J. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"6466","DOI":"10.1039\/D2QO01358D","article-title":"Rescuing the solid-state fluorescence of perylenediimide dyes by host\u2013guest isolation","volume":"9","author":"He","year":"2022","journal-title":"Org. Chem. Front."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"6230","DOI":"10.3390\/molecules18066230","article-title":"Macrocyclic Drugs and Synthetic Methodologies toward Macrocycles","volume":"18","author":"Yu","year":"2013","journal-title":"Molecules"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"659845","DOI":"10.3389\/fchem.2021.659845","article-title":"Macrocycle-Antibiotic Hybrids: A Path to Clinical Candidates","volume":"9","author":"Surur","year":"2021","journal-title":"Front. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.cbpa.2017.02.006","article-title":"Cyclic peptide therapeutics: Past, present and future","volume":"38","author":"Zorzi","year":"2017","journal-title":"Curr. Opin. Chem. Biol."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3477","DOI":"10.1021\/ol006520g","article-title":"A Novel Synthesis of Biaryl-Containing Macrocycles by a Domino Miyaura Arylboronate Formation: Intramolecular Suzuki Reaction","volume":"2","author":"Carbonnelle","year":"2000","journal-title":"Org. Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3099","DOI":"10.1021\/jo202105v","article-title":"Biaryl-Bridged Macrocyclic Peptides: Conformational Constraint via Carbogenic Fusion of Natural Amino Acid Side Chains","volume":"77","author":"Meyer","year":"2012","journal-title":"J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"71","DOI":"10.3762\/bjoc.5.71","article-title":"Ring strain and total syntheses of modified macrocycles of the isoplagiochin type","volume":"5","author":"Speicher","year":"2009","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Sun, D. (2022). Recent Advances in Macrocyclic Drugs and Microwave-Assisted and\/or Solid-Supported Synthesisof Macrocycles. Molecules, 27.","DOI":"10.3390\/molecules27031012"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"4835","DOI":"10.1002\/anie.201913305","article-title":"Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic OxidativeCross-Coupling Reactions","volume":"59","author":"Gaster","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"9355","DOI":"10.1039\/C6CC04466B","article-title":"Crystal structure of a complex between \u03b2-glucopyranose and a macrocyclic receptor with dendritic multicharged water solubilizing chains","volume":"52","author":"Mandal","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"8649","DOI":"10.1039\/C8CC05074K","article-title":"Maltodextrin recognition by a macrocyclic synthetic lectin","volume":"54","author":"Stewart","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"9268","DOI":"10.1039\/D0CC03609A","article-title":"Aqueous recognition of purine and pyrimidine bases by an anthracene-based macrocyclic receptor","volume":"56","author":"Samanta","year":"2020","journal-title":"Chem. Commun."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3514","DOI":"10.1039\/C9OB00592G","article-title":"Oligopeptide-CB[8] complexation with switchable binding pathways","volume":"17","author":"Wu","year":"2019","journal-title":"Org. Biomol. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"8384","DOI":"10.1021\/ja302292c","article-title":"Single-Molecular Artificial Transmembrane Water Channels","volume":"134","author":"Hu","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1025","DOI":"10.1038\/nchem.871","article-title":"Storable, thermally activated, near-infrared chemiluminescent dyes and dye-stained microparticles for optical imaging","volume":"2","author":"Baumes","year":"2010","journal-title":"Nat. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1016\/j.cclet.2020.04.049","article-title":"Supramolecular nano drug delivery systems mediated via host-guest chemistry of cucurbit[n]uril (n = 6 and 7)","volume":"32","author":"Li","year":"2021","journal-title":"Chin. Chem. Lett."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"360","DOI":"10.1080\/10610278.2016.1238473","article-title":"Molecular recognition of nitrogen-containing bases by Zn[5,15-bis-(2,6-dodecyloxyphenyl)]porphyrin","volume":"29","author":"Maltceva","year":"2017","journal-title":"Supramol. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"6719","DOI":"10.1021\/ja00043a016","article-title":"Recognition of Axial Ligands by a Zinc Porphyrin Host on the Basis of Nonpolar Interligand Interaction","volume":"114","author":"Imai","year":"1992","journal-title":"J. Am. Chem. Soc."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/3\/1338\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:19:22Z","timestamp":1760120362000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/3\/1338"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,31]]},"references-count":49,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["molecules28031338"],"URL":"https:\/\/doi.org\/10.3390\/molecules28031338","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,31]]}}}