Advanced search
3 files | 6.79 MB

Chemical classification of cyclic depsipeptides

Lien Taevernier (UGent) , Evelien Wynendaele (UGent) , Bert Gevaert (UGent) and Bart De Spiegeleer (UGent)
Author
Organization
Abstract
Cyclic depsipeptides (CDPs) are a family of cyclic peptide-related compounds, of which the ring is mainly composed of amino- and hydroxy acid residues joined by amide and ester bonds (at least one), leading to a wide diversity of fascinating chemical structures. They differ in both their ring structure and their side chains, especially by the nature of the unusual and non-amino acid building blocks. To date, however, there is no overall uniform chemical classification system available for CDPs and naming of the diverse family members is done rather arbitrarily. Therefore, a broad evaluation of different CDP structures is done, i.e., 1348 naturally occurring CDPs were included, and a straightforward chemical classification system using apparent chemical characteristics is proposed in order to organize the currently scattered CDP data. The overall validity of the classification approach is verified and the compounds categorized in the same groups are considered to be structurally related. This evaluation also revealed that traditionally formed CDP subfamilies, like the dolastatins, might be misleading from a chemical point of view given the structural differences in this subfamily. This up-to-date CDP overview enables peptide and natural product scientists to study the wide diversity in CDP structures, their chemical interrelationships and identification of existing and newly found CDPs. Together with the available information on the species producing these CDPs and their reported biological activities, this paper provides a useful tool to gain new insights into this diverse group of peptides.
Keywords
Cyclic depsipeptides, cyclodepsipeptides, peptolides, romidepsin, cyanopeptolin, CYANOBACTERIUM LYNGBYA-MAJUSCULA, NONRIBOSOMAL PEPTIDE-SYNTHESIS, MARINE CYANOBACTERIUM, NATURAL-PRODUCTS, BIOLOGICAL EVALUATION, CONFORMATIONAL-ANALYSIS, SECONDARY METABOLITES, ELASTASE INHIBITORS, DRUG DISCOVERY, GENE CLUSTERS

Downloads

  • Taevernier PPS 2016.doc
    • full text
    • |
    • open access
    • |
    • application/msword
    • |
    • 194.56 KB
  • Taevernier PPS Fig 2016.doc
    • full text
    • |
    • open access
    • |
    • application/msword
    • |
    • 4.29 MB
  • Taevernier PPS SI 2016.doc
    • full text
    • |
    • open access
    • |
    • application/msword
    • |
    • 2.31 MB

Citation

Please use this url to cite or link to this publication:

Chicago
Taevernier, Lien, Evelien Wynendaele, Bert Gevaert, and Bart De Spiegeleer. 2017. “Chemical Classification of Cyclic Depsipeptides.” Current Protein and Peptide Science 18 (5): 425–452.
APA
Taevernier, L., Wynendaele, E., Gevaert, B., & De Spiegeleer, B. (2017). Chemical classification of cyclic depsipeptides. CURRENT PROTEIN AND PEPTIDE SCIENCE, 18(5), 425–452.
Vancouver
1.
Taevernier L, Wynendaele E, Gevaert B, De Spiegeleer B. Chemical classification of cyclic depsipeptides. CURRENT PROTEIN AND PEPTIDE SCIENCE. 2017;18(5):425–52.
MLA
Taevernier, Lien et al. “Chemical Classification of Cyclic Depsipeptides.” CURRENT PROTEIN AND PEPTIDE SCIENCE 18.5 (2017): 425–452. Print.
@article{8517464,
  abstract     = {Cyclic depsipeptides (CDPs) are a family of cyclic peptide-related compounds, of which the ring is mainly composed of amino- and hydroxy acid residues joined by amide and ester bonds (at least one), leading to a wide diversity of fascinating chemical structures. They differ in both their ring structure and their side chains, especially by the nature of the unusual and non-amino acid building blocks. To date, however, there is no overall uniform chemical classification system available for CDPs and naming of the diverse family members is done rather arbitrarily. Therefore, a broad evaluation of different CDP structures is done, i.e., 1348 naturally occurring CDPs were included, and a straightforward chemical classification system using apparent chemical characteristics is proposed in order to organize the currently scattered CDP data. The overall validity of the classification approach is verified and the compounds categorized in the same groups are considered to be structurally related. This evaluation also revealed that traditionally formed CDP subfamilies, like the dolastatins, might be misleading from a chemical point of view given the structural differences in this subfamily. This up-to-date CDP overview enables peptide and natural product scientists to study the wide diversity in CDP structures, their chemical interrelationships and identification of existing and newly found CDPs. Together with the available information on the species producing these CDPs and their reported biological activities, this paper provides a useful tool to gain new insights into this diverse group of peptides.},
  author       = {Taevernier, Lien and Wynendaele, Evelien and Gevaert, Bert and De Spiegeleer, Bart},
  issn         = {1389-2037},
  journal      = {CURRENT PROTEIN AND PEPTIDE SCIENCE},
  keywords     = {Cyclic depsipeptides,cyclodepsipeptides,peptolides,romidepsin,cyanopeptolin,CYANOBACTERIUM LYNGBYA-MAJUSCULA,NONRIBOSOMAL PEPTIDE-SYNTHESIS,MARINE CYANOBACTERIUM,NATURAL-PRODUCTS,BIOLOGICAL EVALUATION,CONFORMATIONAL-ANALYSIS,SECONDARY METABOLITES,ELASTASE INHIBITORS,DRUG DISCOVERY,GENE CLUSTERS},
  language     = {eng},
  number       = {5},
  pages        = {425--452},
  title        = {Chemical classification of cyclic depsipeptides},
  url          = {http://dx.doi.org/10.2174/1389203717666161128141438},
  volume       = {18},
  year         = {2017},
}

Altmetric
View in Altmetric
Web of Science
Times cited: