Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions
Identifieur interne : 001A68 ( Main/Exploration ); précédent : 001A67; suivant : 001A69Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions
Auteurs : Yoann M. Chabre [Canada] ; Alex Papadopoulos [Canada] ; Alexandre A. Arnold [Canada] ; René Roy [Canada]Source :
- Beilstein Journal of Organic Chemistry [ 1860-5397 ] ; 2014.
Abstract
This paper describes the synthesis of three closely related families of mannopyranoside-containing dendrimers for the purpose of studying subtle structural parameters involved in the measurements of multivalent carbohydrate–protein binding interactions. Toward this goal, two trimers
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DOI: 10.3762/bjoc.10.157
PubMed: 25165490
PubMed Central: 4144466
Affiliations:
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Chabre</name><affiliation wicri:level="4"><nlm:aff id="A1">Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8</nlm:aff><country>Canada</country><wicri:regionArea>Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec</wicri:regionArea><orgName type="university">Université du Québec à Montréal</orgName><placeName><settlement type="city">Montréal</settlement><region type="state">Québec</region></placeName></affiliation></author><author><name sortKey="Papadopoulos, Alex" sort="Papadopoulos, Alex" uniqKey="Papadopoulos A" first="Alex" last="Papadopoulos">Alex Papadopoulos</name><affiliation wicri:level="4"><nlm:aff id="A1">Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8</nlm:aff><country>Canada</country><wicri:regionArea>Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec</wicri:regionArea><orgName type="university">Université du Québec à Montréal</orgName><placeName><settlement type="city">Montréal</settlement><region type="state">Québec</region></placeName></affiliation></author><author><name sortKey="Arnold, Alexandre A" sort="Arnold, Alexandre A" uniqKey="Arnold A" first="Alexandre A" last="Arnold">Alexandre A. Arnold</name><affiliation wicri:level="4"><nlm:aff id="A1">Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8</nlm:aff><country>Canada</country><wicri:regionArea>Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec</wicri:regionArea><orgName type="university">Université du Québec à Montréal</orgName><placeName><settlement type="city">Montréal</settlement><region type="state">Québec</region></placeName></affiliation></author><author><name sortKey="Roy, Rene" sort="Roy, Rene" uniqKey="Roy R" first="René" last="Roy">René Roy</name><affiliation wicri:level="4"><nlm:aff id="A1">Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8</nlm:aff><country>Canada</country><wicri:regionArea>Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec</wicri:regionArea><orgName type="university">Université du Québec à Montréal</orgName><placeName><settlement type="city">Montréal</settlement><region type="state">Québec</region></placeName></affiliation></author></analytic><series><title level="j">Beilstein Journal of Organic Chemistry</title><idno type="eISSN">1860-5397</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><title>Summary</title><p>This paper describes the synthesis of three closely related families of mannopyranoside-containing dendrimers for the purpose of studying subtle structural parameters involved in the measurements of multivalent carbohydrate–protein binding interactions. Toward this goal, two trimers <bold>5</bold> and <bold>9</bold>, three 9-mers <bold>12</bold>, <bold>17</bold>, <bold>21</bold>, and one 27-mer <bold>23</bold>, varying by the number of atoms separating the anomeric and the core carbons, were synthesized using azide–alkyne cycloaddition (CuAAc). Compound <bold>23</bold> was prepared by an efficient convergent strategy. The sugar precursors consisted of either a 2-azidoethyl (<bold>3</bold>) or a prop-2-ynyl α-D-mannopyranoside (<bold>7</bold>) derivative. The solvodynamic diameters of 9-mer <bold>12</bold>, <bold>17</bold>, and <bold>21</bold> were determined by pulsed-field-gradient-stimulated echo (PFG-STE) NMR experiments and were found to be 3.0, 2.5, and 3.4 nm, respectively.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Roy, R" uniqKey="Roy R">R Roy</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kiessling, L L" uniqKey="Kiessling L">L L Kiessling</name></author><author><name sortKey="Gestwicki, J E" uniqKey="Gestwicki J">J E Gestwicki</name></author><author><name sortKey="Strong, L E" uniqKey="Strong L">L E Strong</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Imberty, A" uniqKey="Imberty A">A Imberty</name></author><author><name sortKey="Chabre, Y M" uniqKey="Chabre Y">Y M Chabre</name></author><author><name sortKey="Roy, R" uniqKey="Roy R">R 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M">M G Finn</name></author><author><name sortKey="Fokin, V V" uniqKey="Fokin V">V V Fokin</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Corbell, J B" uniqKey="Corbell J">J B Corbell</name></author><author><name sortKey="Lundquist, J J" uniqKey="Lundquist J">J J Lundquist</name></author><author><name sortKey="Toone, E J" uniqKey="Toone E">E J Toone</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Talga, M L" uniqKey="Talga M">M L Talga</name></author><author><name sortKey="Fan, N" uniqKey="Fan N">N Fan</name></author><author><name sortKey="Fueri, A L" uniqKey="Fueri A">A L Fueri</name></author><author><name sortKey="Brown, R K" uniqKey="Brown R">R K Brown</name></author><author><name sortKey="Chabre, Y M" uniqKey="Chabre Y">Y M Chabre</name></author><author><name sortKey="Bandyopadhyay, P" uniqKey="Bandyopadhyay P">P Bandyopadhyay</name></author><author><name sortKey="Roy, R" uniqKey="Roy R">R Roy</name></author><author><name sortKey="Dam, T K" uniqKey="Dam T">T K Dam</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wu, D H" uniqKey="Wu D">D H Wu</name></author><author><name sortKey="Chen, A D" uniqKey="Chen A">A D Chen</name></author><author><name sortKey="Johnson, C S" uniqKey="Johnson C">C S Johnson</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Holz, M" uniqKey="Holz M">M Holz</name></author><author><name sortKey="Weing Rtner, H" uniqKey="Weing Rtner H">H Weingärtner</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Van Beek, J D" uniqKey="Van Beek J">J D van Beek</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Canada</li></country><region><li>Québec</li></region><settlement><li>Montréal</li></settlement><orgName><li>Université du Québec à Montréal</li></orgName></list><tree><country name="Canada"><region name="Québec"><name sortKey="Chabre, Yoann M" sort="Chabre, Yoann M" uniqKey="Chabre Y" first="Yoann M" last="Chabre">Yoann M. Chabre</name></region><name sortKey="Arnold, Alexandre A" sort="Arnold, Alexandre A" uniqKey="Arnold A" first="Alexandre A" last="Arnold">Alexandre A. Arnold</name><name sortKey="Papadopoulos, Alex" sort="Papadopoulos, Alex" uniqKey="Papadopoulos A" first="Alex" last="Papadopoulos">Alex Papadopoulos</name><name sortKey="Roy, Rene" sort="Roy, Rene" uniqKey="Roy R" first="René" last="Roy">René Roy</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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