Journal
SCIENCE
Volume 301, Issue 5637, Pages 1219-1220Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1086644
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- NIGMS NIH HHS [GM 27932] Funding Source: Medline
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Alkanes adopt extended conformations in solution that minimize steric interactions and maximize surface area. Folding can reduce the amount of hydrophobic surface exposed to solvent, but sterically unfavorable gauche interactions result. However, we found that the alkyl chains of two common surfactants in aqueous solution adopt helical conformations when bound within a synthetic receptor. The receptor recognizes the helical alkane better than the extended conformation, even though 2 to 3 kilocalories per mole of strain is introduced. The proper filling of space and burial of hydrophobic surface drive the molecular recognition between the receptor and the coiled alkane.
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