Depsipeptide

Source: Wikipedia, the free encyclopedia.

A depsipeptide is a peptide in which one or more of its amide, -C(O)NHR-, groups are replaced by the corresponding ester, -C(O)OR-.[1] Many depsipeptides have both peptide and ester linkages.[2] Elimination of the N–H group in a peptide structure results in a decrease of H-bonding capability, which is responsible for secondary structure and folding patterns of peptides, thus inducing structural deformation of the helix and β-sheet structures.[2][3] Because of decreased resonance delocalization in esters relative to amides, depsipeptides have lower rotational barriers for cis-trans isomerization and therefore they have more flexible structures than their native analogs.[2][3] They are mainly found in marine and microbial natural products.[4]

Example of a depsipeptide with 3 amide groups (highlighted blue) and one ester group (highlighted green). R1 and R3 are organic groups (e. g. methyl) or a hydrogen atom found in α-hydroxycarboxylic acids. R2, R4 and R5 are organic groups or a hydrogen atom found in common amino acids.

Depsipeptide natural products

Enterochelin is a depsipeptide that is an iron-transporter.[5]

Several depsipeptides have been found to exhibit anti-cancer properties.[6]

A depsipeptide enzyme inhibitor includes romidepsin, a member of the bicyclic peptide class, a known histone deacetylase inhibitors (HDACi). It was first isolated as a fermentation product from Chromobacterium violaceum by the Fujisawa Pharmaceutical Company.[7]

ClpP) to initiate uncontrolled peptide and unfolded protein degradation, killing many Gram-positive bacteria.[11][12][13]

Depsipeptides can be formed through a Passerini reaction.[14]

References

  1. doi:10.1351/goldbook.D01604
  2. ^
    PMID 21452874
    .
  3. ^
    PMID 24626261
    .
  4. PMID 16351050
    .
  5. doi:10.1021/cr00105a003
    .
  6. S2CID 22071968
    .
  7. PMID 17958342
    .
  8. PMID 20339399
    .
  9. ^ K. H. Michel, R. E. Kastner (Eli Lilly and Company), US 4492650, 1985 [Chem. Abstr. 1985, 102, 130459]
  10. PMID 1778798
    .
  11. PMID 20851345
    .
  12. S2CID 36525372
    .
  13. PMID 24422534
    .
  14. ISBN 978-3-030-50864-7
    , retrieved 2022-10-26

Further reading
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