Using click chemistry to access mono- and ditopic β-cyclodextrin hosts substituted by chiral amino acids

被引：19
|
作者：
Tran, Diem Ngan [1 ,2 ]
Blaszkiewicz, Claire [1 ,2 ]
Menuel, Stephane [1 ,2 ]
Roucoux, Alain [3 ]
Philippot, Karine [4 ]
Hapiot, Frederic [1 ,2 ]
Monflier, Eric [1 ,2 ]
机构：
[1] Univ Lille Nord France, F-59000 Lille, France
[2] UArtois, UCCS, CNRS, UMR 8181, F-62300 Lens, France
[3] Univ Europeenne Bretagne, Ecole Natl Super Chim Rennes, CNRS, UMR 6226, F-35708 Rennes 7, France
[4] Univ Toulouse, UPS, INPT, CNRS,LCC, F-31077 Toulouse, France
来源：
CARBOHYDRATE RESEARCH | 2011年 / 346卷 / 02期
关键词：
Cyclodextrins; Azides; Amino acids; Cycloaddition; Chirality; DERIVATIVES; MICROWAVES; COMPLEXES;
D O I：
10.1016/j.carres.2010.11.024
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A wide range of chiral mono- and ditopic cyclodextrin-based receptors have been synthesized by Cul-catalyzed azide-alkyne cycloaddition starting from mono-6-azido-beta-cyclodextrin and chiral amino acids. Of interest, microwaves proved very efficient to access a wide range of ditopic p-cyclodextrin receptors with quantitative yields. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：210 / 218
页数：9
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  • [1] Easily Accessible Mono- and Polytopic β-Cyclodextrin Hosts by Click Chemistry
    Mourer, Maxime
    Hapiot, Frederic
    Tilloy, Sebastien
    Monflier, Eric
    Menuel, Stephane
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (34) : 5723 - 5730
  • [2] FACILE SYNTHESIS OF MONO- AND POLYTOPIC β-CYCLODEXTRIN AROMATIC ALDEHYDES BY CLICK CHEMISTRY
    Guo, Hongyu
    Yang, Fafu
    Zhang, Yingmei
    Di, Xingdong
    [J]. SYNTHETIC COMMUNICATIONS, 2015, 45 (03) : 338 - 347
  • [3] Chiral separation of dansyl amino acids in capillary electrophoresis using mono-(3-methylimidazolium)-β-cyclodextrin chloride as selector
    Tang, Weihua
    Ong, Teng Teng
    Ng, Siu-Choon
    [J]. JOURNAL OF SEPARATION SCIENCE, 2007, 30 (09) : 1343 - 1349
  • [4] Mono-, Di-, or Triazidated Cyclodextrin-Based Polyrotaxanes for Facile and Efficient Functionalization via Click Chemistry
    Hyun, Hoon
    Yui, Nobuhiko
    [J]. MACROMOLECULAR RAPID COMMUNICATIONS, 2011, 32 (03) : 326 - 331
  • [5] Mono- and ditopic models of binding of a photochromic chromene annelated with an 18-crown-6 ether with protonated amino acids
    Paramonov, Sergey V.
    Fedorov, Yury
    Lokshin, Vladimir
    Tulyakova, Elena
    Vermeersch, Gaston
    Delbaere, Stephanie
    Fedorova, Olga
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (03) : 671 - 682
  • [6] Chiral separation of dansyl amino acids in capillary electrophoresis using mono-(3-methyl-imidazolium)-β-cyclodextrin chloride as a selector (vol 30, pg 1343, 2007)
    Tang, Weihua
    Ong, Teng Teng
    Ng, Siu-Choon
    [J]. JOURNAL OF SEPARATION SCIENCE, 2007, 30 (11) : 1806 - 1806
  • [7] Click Chemistry Inspired Synthesis of Novel Ferrocenyl-Substituted Amino Acids or Peptides
    Sudhir, V. Sai
    Venkateswarlu, Ch.
    Musthafa, O. T. Muhammed
    Sampath, S.
    Chandrasekaran, Srinivasan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (13) : 2120 - 2129
  • [8] Synthesis of α-substituted β-amino acids using pseudoephedrine as a chiral auxiliary
    Nagula, G
    Huber, VJ
    Lum, C
    Goodman, BA
    [J]. ORGANIC LETTERS, 2000, 2 (22) : 3527 - 3529
  • [9] Chiral Separation of Catechin by Capillary Electrophoresis Using Mono-, Di-, Tri-succinyl-β-cyclodextrin as Chiral Selectors
    Kim, Hyunmyung
    Choi, Youngjin
    Lim, Jun
    Paik, Seung-R
    Jung, Seunho
    [J]. CHIRALITY, 2009, 21 (10) : 937 - 942
  • [10] Stereoselective α-alkylation of new chiral auxiliaries:: An access to enantiomerically pure α- and α,β-substituted β-amino acids
    Agami, C
    Cheramy, S
    Dechoux, L
    [J]. SYNLETT, 1999, (11) : 1838 - 1840
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