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  • 标题:From reactants to products via simple hydrogen-bonding networks: Information transmission in chemical reactions
  • 本地全文:下载
  • 作者:Giuseppe Brancato ; Frédéric Coutrot ; David A. Leigh
  • 期刊名称:Proceedings of the National Academy of Sciences
  • 印刷版ISSN:0027-8424
  • 电子版ISSN:1091-6490
  • 出版年度:2002
  • 卷号:99
  • 期号:8
  • 页码:4967-4971
  • DOI:10.1073/pnas.072695799
  • 语种:English
  • 出版社:The National Academy of Sciences of the United States of America
  • 摘要:The transmission of information is ubiquitous in nature and often occurs through supramolecular hydrogen bonding processes. Here we report that there is a remarkable correlation during synthesis between the efficiency of the hydrogen-bond-directed assembly of peptide-based [2]rotaxanes and the symmetry distortion of the macrocycle in the structure of the final product. It transpires that the ability of the flexible macrocycle-precursor to wrap around an unsymmetrical hydrogen bonding template affects both the reaction yield and a quantifiable measure of the symmetry distortion of the macrocycle in the product. When the yields of peptide rotaxane-forming reactions are high, so is the symmetry distortion in the macrocycle; when the yields are low, indicating a poor fit between the components, the macrocycle symmetry is relatively unaffected by the thread. Thus during a synthetic sequence, as in complex biological assembly processes, hydrogen bonding can code and transmit "information"--in this case a distortion from symmetry--between chemical entities by means of a supramolecularly driven multicomponent assembly process. If this phenomenon is general, it could have far reaching consequences for the use of supramolecular-directed reactions in organic chemistry.
  • 关键词:continuous symmetry measure‖hydrogen bonds‖molecular recognition‖rotaxanes‖symmetry distortion
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