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Fe(III) coordination properties of two new saccharide-based enterobactin analogues: methyl 2,3,4-tris-O-[N-[2,3-di(hydroxy)benzoyl-glycyl]-aminopropyl]-alpha-D-glucopyranoside and methyl 2,3,4-tris-O-[N-[2,3-di-(hydroxy)-benzoyl]-aminopropyl]-alpha-D-glucopyranoside.

Publication ,  Journal Article
Dhungana, S; Heggemann, S; Heinisch, L; Möllmann, U; Boukhalfa, H; Crumbliss, AL
Published in: Inorganic chemistry
December 2001

The synthesis of two saccharide-based enterobactin analogues, methyl 2,3,4-tris-O[-N[2,3-di(hydroxy)benzoyl-glycyl]-aminopropyl]-alpha-D-glucopyranoside (H(6)L(A)) and methyl 2,3,4-tris-O-[N-[2,3-di(hydroxy)benzoyl]-aminopropyl]-alpha-D-glucopyranoside (H(6)L(B)), are reported along with their pK(a) values, Fe(III) binding constants, and aqueous solution speciation as determined by spectrophotometric and potentiometric titration techniques. Use of a saccharide platform to synthesize a hexadentate triscatechol chelator provides some advantages over other approaches to enterobactin models, including significant water solubility, resistance to hydrolysis, and backbone chirality which may provide favorable recognition and availability to cells. The protonation constants for the catechol ligand hydroxyl moieties were determined for both ligands and found to be significantly different, which is attributed to the differences in the spacer chain of the two triscatechols. Proton dependent Fe(III)-ligand equilibrium constants were determined using a model involving the sequential protonation of the Fe(III)-ligand complex. These results were used to calculate the formation constants, log beta(110) = 41.38 for Fe(III)-H(6)L(A) and log beta(110) = 46.38 for Fe(III)-H(6)L(B). The calculated pM values of 28.6 for H(6)L(A) and 28.3 for H(6)L(B) indicate that these ligands possess Fe(III) affinities comparable to or greater than other enterobactin models and are thermodynamically capable of removing Fe(III) from transferrin.

Duke Scholars

Published In

Inorganic chemistry

DOI

EISSN

1520-510X

ISSN

0020-1669

Publication Date

December 2001

Volume

40

Issue

27

Start / End Page

7079 / 7086

Related Subject Headings

  • Spectrophotometry, Ultraviolet
  • Spectrometry, Mass, Electrospray Ionization
  • Siderophores
  • Salicylates
  • Nuclear Magnetic Resonance, Biomolecular
  • Molecular Structure
  • Ligands
  • Iron
  • Inorganic & Nuclear Chemistry
  • Glucosides
 

Citation

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Chicago
ICMJE
MLA
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Dhungana, S., S. Heggemann, L. Heinisch, U. Möllmann, H. Boukhalfa, and A. L. Crumbliss. “Fe(III) coordination properties of two new saccharide-based enterobactin analogues: methyl 2,3,4-tris-O-[N-[2,3-di(hydroxy)benzoyl-glycyl]-aminopropyl]-alpha-D-glucopyranoside and methyl 2,3,4-tris-O-[N-[2,3-di-(hydroxy)-benzoyl]-aminopropyl]-alpha-D-glucopyranoside.Inorganic Chemistry 40, no. 27 (December 2001): 7079–86. https://doi.org/10.1021/ic0104003.
Journal cover image

Published In

Inorganic chemistry

DOI

EISSN

1520-510X

ISSN

0020-1669

Publication Date

December 2001

Volume

40

Issue

27

Start / End Page

7079 / 7086

Related Subject Headings

  • Spectrophotometry, Ultraviolet
  • Spectrometry, Mass, Electrospray Ionization
  • Siderophores
  • Salicylates
  • Nuclear Magnetic Resonance, Biomolecular
  • Molecular Structure
  • Ligands
  • Iron
  • Inorganic & Nuclear Chemistry
  • Glucosides