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Synthesis and Binding of Mannose-Specific Synthetic Carbohydrate Receptors.
Bravo, M Fernando; Palanichamy, Kalanidhi; Shlain, Milan A; Schiro, Frank; Naeem, Yasir; Marianski, Mateusz; Braunschweig, Adam B.
  • Bravo MF; Advanced Science Research Center at the Graduate Center, City University of New York, 85 St Nicholas Terrace, New York, NY, 10031, USA.
  • Palanichamy K; Department of Chemistry and Biochemistry, Hunter College, 695 Park Ave, New York, NY, 10065, USA.
  • Shlain MA; The PhD Program in Chemistry, The Graduate Center of the, City University of New York, 365 5th Ave, New York, NY, 10016, USA.
  • Schiro F; Advanced Science Research Center at the Graduate Center, City University of New York, 85 St Nicholas Terrace, New York, NY, 10031, USA.
  • Naeem Y; Department of Chemistry and Biochemistry, Hunter College, 695 Park Ave, New York, NY, 10065, USA.
  • Marianski M; Advanced Science Research Center at the Graduate Center, City University of New York, 85 St Nicholas Terrace, New York, NY, 10031, USA.
  • Braunschweig AB; Department of Chemistry and Biochemistry, Hunter College, 695 Park Ave, New York, NY, 10065, USA.
Chemistry ; 26(51): 11782-11795, 2020 Sep 10.
Article in English | MEDLINE | ID: covidwho-777429
ABSTRACT
Synthetic carbohydrate receptors (SCRs) that selectively recognize cell-surface glycans could be used for detection, drug delivery, or as therapeutics. Here we report the synthesis of seven new C2h symmetric tetrapodal SCRs. The structures of these SCRs possess a conserved biaryl core, and they vary in the four heterocyclic binding groups that are linked to the biaryl core via secondary amines. Supramolecular association between these SCRs and five biologically relevant C1 -O-octyloxy glycans, α/ß-glucoside (α/ß-Glc), α/ß-mannoside (α/ß-Man), and ß-galactoside (ß-Gal), was studied by mass spectrometry, 1 H NMR titrations, and molecular modeling. These studies revealed that selectivity can be achieved in these tetrapodal SCRs by varying the heterocyclic binding group. We found that SCR017 (3-pyrrole), SCR021 (3-pyridine), and SCR022 (2-phenol) bind only to ß-Glc. SCR019 (3-indole) binds only to ß-Man. SCR020 (2-pyridine) binds ß-Man and α-Man with a preference to the latter. SCR018 (2-indole) binds α-Man and ß-Gal with a preference to the former. The glycan guests bound within their SCR hosts in one of three supramolecular geometries center-parallel, center-perpendicular, and off-center. Many host-guest combinations formed higher stoichiometry complexes, 21 glycan⋅SCR or 12 glycan⋅SCR, where the former are driven by positive allosteric cooperativity induced by glycan-glycan contacts.
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Full text: Available Collection: International databases Database: MEDLINE Main subject: Polysaccharides / Carbohydrates / Receptors, Cell Surface / Lectins, C-Type / Mannose-Binding Lectins / Receptors, Artificial / Mannose Type of study: Experimental Studies / Randomized controlled trials Language: English Journal: Chemistry Journal subject: Chemistry Year: 2020 Document Type: Article Affiliation country: Chem.202000481

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Full text: Available Collection: International databases Database: MEDLINE Main subject: Polysaccharides / Carbohydrates / Receptors, Cell Surface / Lectins, C-Type / Mannose-Binding Lectins / Receptors, Artificial / Mannose Type of study: Experimental Studies / Randomized controlled trials Language: English Journal: Chemistry Journal subject: Chemistry Year: 2020 Document Type: Article Affiliation country: Chem.202000481