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Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks.

Publication ,  Journal Article
Walsh, CT; Malcolmson, SJ; Young, TS
Published in: ACS chemical biology
March 2012

Nitrogen heterocycles are the key functional and structural elements in both RNA and DNA, in half a dozen of the most important coenzymes, and in many synthetic drug scaffolds. On the other hand, only 3 of 20 proteinogenic amino acids have nitrogen heterocycles: proline, histidine, and tryptophan. This inventory can be augmented in microbial proteins by posttranslational modifications downstream of leader peptide regions that convert up to 10 serine, threonine, and cysteine residues, side chains and peptide backbones, into oxazoles, thiazoles, and pyridine rings. Subsequent proteolysis releases these heterocyclic scaffolds in both linear and macrocyclic frameworks as bioactive small molecules.

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Published In

ACS chemical biology

DOI

EISSN

1554-8937

ISSN

1554-8929

Publication Date

March 2012

Volume

7

Issue

3

Start / End Page

429 / 442

Related Subject Headings

  • Tryptophan
  • Thiazoles
  • Pyridines
  • Proteins
  • Protein Processing, Post-Translational
  • Proline
  • Oxazoles
  • Organic Chemistry
  • Histidine
  • 34 Chemical sciences
 

Citation

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Walsh, C. T., Malcolmson, S. J., & Young, T. S. (2012). Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks. ACS Chemical Biology, 7(3), 429–442. https://doi.org/10.1021/cb200518n
Walsh, Christopher T., Steven J. Malcolmson, and Travis S. Young. “Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks.ACS Chemical Biology 7, no. 3 (March 2012): 429–42. https://doi.org/10.1021/cb200518n.
Walsh CT, Malcolmson SJ, Young TS. Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks. ACS chemical biology. 2012 Mar;7(3):429–42.
Walsh, Christopher T., et al. “Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks.ACS Chemical Biology, vol. 7, no. 3, Mar. 2012, pp. 429–42. Epmc, doi:10.1021/cb200518n.
Walsh CT, Malcolmson SJ, Young TS. Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks. ACS chemical biology. 2012 Mar;7(3):429–442.
Journal cover image

Published In

ACS chemical biology

DOI

EISSN

1554-8937

ISSN

1554-8929

Publication Date

March 2012

Volume

7

Issue

3

Start / End Page

429 / 442

Related Subject Headings

  • Tryptophan
  • Thiazoles
  • Pyridines
  • Proteins
  • Protein Processing, Post-Translational
  • Proline
  • Oxazoles
  • Organic Chemistry
  • Histidine
  • 34 Chemical sciences