Abstract

Synthetic or model receptors for biorelevant targets are proposed as a means of evaluating intermolecular forces. The systems involve the use of U-shaped molecular modules which are combined with appropriate spacer elements to provide cleft-like concave structures. These feature convergent functional groups, complementary to the convex surfaces of the targets. Peripheral functions provide a range of solubilities for determination of hydrogen bonding, stacking and van der Waals forces in a variety of solvents. Target structure include heterocyclics, amino acids, peptides and metal ions. Asymmetric microenvironments are also proposed for enantioselective recognition and the control for stereochemistry.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM027932-13
Application #
3275172
Study Section
Bio-Organic and Natural Products Chemistry Study Section (BNP)
Project Start
1980-04-01
Project End
1996-03-31
Budget Start
1993-04-01
Budget End
1994-03-31
Support Year
13
Fiscal Year
1993
Total Cost
Indirect Cost

  Institution

Name
Massachusetts Institute of Technology
Department
Type
Schools of Arts and Sciences
DUNS #
City
Cambridge
State
MA
Country
United States
Zip Code
02139

  Publications

Ajami, Dariush; Rebek, Julius (2012) Reversibly expanded encapsulation complexes. Top Curr Chem 319:57-78
Sather, Aaron C; Berryman, Orion B; Rebek Jr, Julius (2012) Synthesis of fused indazole ring systems and application to nigeglanine hydrobromide. Org Lett 14:1600-3
Durola, Fabien; Dube, Henry; Ajami, Dariush et al. (2011) Control of Nanospaces with Molecular Devices. Supramol Chem 23:37-41
Lledo, Agusti; Kamioka, Seiji; Sather, Aaron C et al. (2011) Supramolecular architecture with a cavitand-capsule chimera. Angew Chem Int Ed Engl 50:1299-301
Berryman, Orion B; Dube, Henry; Rebek Jr, Julius (2011) Photophysics Applied to Cavitands and Capsules. Isr J Chem 51:700-709
Berryman, Orion B; Sather, Aaron C; Rebek Jr, Julius (2011) A deep cavitand with a fluorescent wall functions as an ion sensor. Org Lett 13:5232-5
Xiao, Shengxiong; Ajami, Dariush; Rebek Jr, Julius (2010) An extended cavitand with an introverted carboxylic acid. Chem Commun (Camb) 46:2459-61
Durola, Fabien; Rebek Jr, Julius (2010) The ouroborand: a cavitand with a coordination-driven switching device. Angew Chem Int Ed Engl 49:3189-91
Busseron, Eric; Rebek Jr, Julius (2010) Guest recognition in a partially bridged deep cavitand. Org Lett 12:4828-31
Pinacho Crisostomo, Fernando R; Lledo, Agusti; Shenoy, Siddhartha R et al. (2009) Recognition and organocatalysis with a synthetic cavitand receptor. J Am Chem Soc 131:7402-10

Showing the most recent 10 out of 40 publications