This application seeks continued support for studies of synthetic molecular assemblies. The assemblies are reversibly formed dimers of self-complementary molecules and are held together through weak intermolecular forces. The assemblies become closed-shell structures that act to encapsulate smaller molecules. The syntheses of these capsules of various sizes, shapes and solubilities are proposed and the behavior of their assemblies are to be determined. The specific issues to be addressed involve the effects of functional groups on guest binding; dynamic processes such as rates into and out of the capsules and molecular motions within the capsule by the guest; the use of the capsules as reaction chambers to catalyze rearrangements; the capacities of the capsules as asymmetric microenvironments, and their use as sensors or signaling devices. Many of the phenomena observed with these synthetic systems mimic those of naturally occurring assemblies such as allosteric enzymes and viral coat proteins. It is hoped that the rules governing the assembly process and the phenomena such as selection, transport and catalysis which owe their existence to the assembly, can be deciphered with the synthetic systems.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM050174-06
Application #
2734748
Study Section
Bio-Organic and Natural Products Chemistry Study Section (BNP)
Project Start
1993-12-01
Project End
2001-06-30
Budget Start
1998-07-01
Budget End
1999-06-30
Support Year
6
Fiscal Year
1998
Total Cost
Indirect Cost
Name
Scripps Research Institute
Department
Type
DUNS #
City
La Jolla
State
CA
Country
United States
Zip Code
92037
Hooley, Richard J; Rebek Jr, Julius (2009) Chemistry and catalysis in functional cavitands. Chem Biol 16:255-64
Restorp, Per; Berryman, Orion B; Sather, Aaron C et al. (2009) A synthetic receptor for hydrogen-bonding to fluorines of trifluoroborates. Chem Commun (Camb) :5692-4
Hooley, Richard; Shenoy, Siddhartha; Rebek Jr, Julius (2008) Electronic and Steric Effects in Binding of Deep Cavitands. Org Lett :
Lledo, Agusti; Hooley, Richard J; Rebek Jr, Julius (2008) Recognition of guests by water-stabilized cavitand hosts. Org Lett 10:3669-71
Podkoscielny, Dagmara; Hooley, Richard J; Rebek Jr, Julius et al. (2008) Ferrocene derivatives included in a water-soluble cavitand: are they electroinactive? Org Lett 10:2865-8
Restorp, Per; Rebek Jr, Julius (2008) Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates. J Am Chem Soc 130:11850-1
Barrett, Elizabeth S; Dale, Trevor J; Rebek Jr, Julius (2008) Stability, dynamics, and selectivity in the assembly of hydrogen-bonded hexameric capsules. J Am Chem Soc 130:2344-50
Iwasawa, Tetsuo; Wash, Paul; Gibson, Christoph et al. (2007) Reaction of an Introverted Carboxylic Acid with Carbodiimide. Tetrahedron 63:6506-6511
Ajami, Dariush; Rebek Jr, Julius (2007) Adaptations of guest and host in expanded self-assembled capsules. Proc Natl Acad Sci U S A 104:16000-3
Barrett, Elizabeth S; Dale, Trevor J; Rebek Jr, Julius (2007) Assembly and exchange of resorcinarene capsules monitored by fluorescence resonance energy transfer. J Am Chem Soc 129:3818-9

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