Format

Send to

Choose Destination
See comment in PubMed Commons below
J Org Chem. 2008 Apr 18;73(8):3205-11. doi: 10.1021/jo800129j. Epub 2008 Mar 20.

Preparation and multivalently enhanced guest-binding affinity of water-soluble cyclophane heptadecamers.

Author information

1
Institute for Materials Chemistry and Engineering, Kyushu University, Moto-oka 744, Fukuoka 819-0395, Japan. ohaya@ms.ifoc.kyushu-u.ac.jp

Abstract

Water-soluble cyclophane heptadecamers (17a and 17b), which were constructed with the core cyclophane heptadecamer and 36 polar side chains with a terminal galactose or glucose residue, respectively, were prepared. An analogous cyclophane pentamer (5a) was also prepared. The stoichiometry for the complex of the cyclophane oligomers with fluorescence guests such as TNS was confirmed to be 1:1 host:guest by a Job plot. The guest-binding affinity of cyclophane heptadecamers 17a and 17b was much enhanced relative to that of a corresponding monocyclic cyclophane (1a), i.e., the 1:1 binding constant (K) values for 17a with TNS, 2,6-ANS, and 1,8-ANS were ca. 1700-, 1600-, and 1500-fold larger than those of 1a for the identical guests, respectively, which reflects the multivalency effects in macrocycles. Meanwhile, the corresponding K values for the cyclophane pentamer 5a with TNS, 2,6-ANS, and 1,8-ANS were ca. 250-, 250-, and 110-fold larger than those of 1a for the identical guest, respectively.

PMID:
18351779
DOI:
10.1021/jo800129j
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society
    Loading ...
    Support Center