Synthesis and structure of chiral macrocycles containing 2,2'-bipyridine subunits

R. Bruce Hopkins, Jeffrey S. Albert, Donna Van Engen, Andrew Hamilton

Research output: Contribution to journalArticle

Abstract

A series of macrocyclic receptors has been prepared containing bipyridine groups linked to two amino acids. Variations in both the amino acid and the linking spacer have been made. The structure of the resulting macrocycles has been investigated using 1H NMR spectroscopy and X-ray crystallography. The use of L-valine leads to an open conformation for the macrocycle in which the 2-propyl substituents are directed perpendicular to the plane of the ring leaving the bipyridine and amide groups accessible for binding to a metal or complementary substrate. Proline-based macrocycles take up a twisted arrangement with the linking chain stretched across the face of the bipyridine which takes up a trans conformation. The metal ion binding properties of these derivatives have been investigated and shown to occur only to the valine macrocyles which have the two pyridine rings preorganized for complexation. These macrocycles have also been shown to bind to phenolic hydroxyl groups by using hydrogen-bond donors and acceptors from the amide groups in the linking chain.

Original languageEnglish (US)
Pages (from-to)1121-1128
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume4
Issue number7
DOIs
StatePublished - Jul 1996

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2,2'-Dipyridyl
Valine
Amides
Conformations
Metals
Amino Acids
X ray crystallography
X Ray Crystallography
Complexation
Proline
Hydroxyl Radical
Nuclear magnetic resonance spectroscopy
Metal ions
Hydrogen
Hydrogen bonds
Magnetic Resonance Spectroscopy
Ions
Derivatives
Substrates
pyridine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Synthesis and structure of chiral macrocycles containing 2,2'-bipyridine subunits. / Hopkins, R. Bruce; Albert, Jeffrey S.; Van Engen, Donna; Hamilton, Andrew.

In: Bioorganic and Medicinal Chemistry, Vol. 4, No. 7, 07.1996, p. 1121-1128.

Research output: Contribution to journalArticle

Hopkins, R. Bruce ; Albert, Jeffrey S. ; Van Engen, Donna ; Hamilton, Andrew. / Synthesis and structure of chiral macrocycles containing 2,2'-bipyridine subunits. In: Bioorganic and Medicinal Chemistry. 1996 ; Vol. 4, No. 7. pp. 1121-1128.
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