Skip to main content
construction release_alert
Scholars@Duke will be undergoing maintenance April 11-15. Some features may be unavailable during this time.
cancel
Journal cover image

Crystal and molecular structures of ionophore-siderophore host-guest supramolecular assemblies relevant to molecular recognition.

Publication ,  Journal Article
Dhungana, S; White, PS; Crumbliss, AL
Published in: Journal of the American Chemical Society
December 2003

Ionophore-siderophore host-guest assemblies composed of 18-crown-6 and ferrioxamine B, benzo-18-crown-6 and ferrioxamine B, and cis-syn-cis-dicyclohexano-18-crown-6 and ferrioxamine B were successfully crystallized, and their structures were determined by single-crystal X-ray diffraction. All three crystal lattices also include solvated Mg(II) and perchlorate ions. The ionophore-siderophore host-guest assembly is noncovalently held together by a hydrogen bonding interaction between the pendant protonated amine in the second coordination sphere of ferrioxamine B and the hydrogen bond acceptor oxygen atoms in the crown ether. The crystals of 18-crown-6:ferrioxamine B host-guest assembly are monoclinic, with space group P2(1)/c, and four molecules per unit cell with dimensions a = 19.8327(11) A, b = 20.4111(11) A, c = 15.1698(8) A, and beta = 96.435(1) degrees. The crystals of benzo-18-crown-6:ferrioxamine B host-guest assembly are triclinic, with space group P(-)1, and two molecules per unit cell with dimensions a = 11.1747(10) A, b = 16.0580(15) A, c = 18.4175(17) A, alpha = 80.469(3) degrees, beta = 81.481(3) degrees and gamma = 70.212(2) degrees. The crystals of cis-syn-cis-dicyclohexano-18-crown-6:ferrioxamine B host-guest assembly are monoclinic, with space group P2(1)/c, and four molecules per unit cell with dimensions a = 20.1473(13) A, b = 21.5778(15) A, c = 14.8013(10) A, and beta = 94.586(2) degrees. The crystal structures of all three host-guest assemblies contain a racemic mixture of Lambda-N-cis, cis and Delta-N-cis, cis coordination isomers of ferrioxamine B. The crystal structures indicate that the steric rigidity of the benzo-18-crown-6 and cis-syn-cis-dicyclohexano-18-crown-6 cavity has a pronounced effect on the conformation of the crown ring and ultimately on the hydrogen bonding interactions between the crown ethers and ferrioxamine B. The structural parameters and the conformational features of the ferrioxamine B guests compare very well with each other and with those of the ferrioxamine B structure obtained in the absence of a host. Structural features relevant to siderophore molecular recognition are discussed.

Duke Scholars

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

December 2003

Volume

125

Issue

48

Start / End Page

14760 / 14767

Related Subject Headings

  • Siderophores
  • Models, Molecular
  • Ionophores
  • Hydrogen Bonding
  • General Chemistry
  • Ferric Compounds
  • Deferoxamine
  • Crystallography, X-Ray
  • Crown Ethers
  • 40 Engineering
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Dhungana, S., White, P. S., & Crumbliss, A. L. (2003). Crystal and molecular structures of ionophore-siderophore host-guest supramolecular assemblies relevant to molecular recognition. Journal of the American Chemical Society, 125(48), 14760–14767. https://doi.org/10.1021/ja035778+
Dhungana, Suraj, Peter S. White, and Alvin L. Crumbliss. “Crystal and molecular structures of ionophore-siderophore host-guest supramolecular assemblies relevant to molecular recognition.Journal of the American Chemical Society 125, no. 48 (December 2003): 14760–67. https://doi.org/10.1021/ja035778+.
Dhungana S, White PS, Crumbliss AL. Crystal and molecular structures of ionophore-siderophore host-guest supramolecular assemblies relevant to molecular recognition. Journal of the American Chemical Society. 2003 Dec;125(48):14760–7.
Dhungana, Suraj, et al. “Crystal and molecular structures of ionophore-siderophore host-guest supramolecular assemblies relevant to molecular recognition.Journal of the American Chemical Society, vol. 125, no. 48, Dec. 2003, pp. 14760–67. Epmc, doi:10.1021/ja035778+.
Dhungana S, White PS, Crumbliss AL. Crystal and molecular structures of ionophore-siderophore host-guest supramolecular assemblies relevant to molecular recognition. Journal of the American Chemical Society. 2003 Dec;125(48):14760–14767.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

December 2003

Volume

125

Issue

48

Start / End Page

14760 / 14767

Related Subject Headings

  • Siderophores
  • Models, Molecular
  • Ionophores
  • Hydrogen Bonding
  • General Chemistry
  • Ferric Compounds
  • Deferoxamine
  • Crystallography, X-Ray
  • Crown Ethers
  • 40 Engineering