depsipeptide
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A depsipeptide is a peptide in which one or more amide, -C(O)NHR-, linkages are replaced by the corresponding ester, -C(O)OR-. Many depsipeptides have both peptide and ester linkages. 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. Because of decreased resonance delocalization in esters relative to amides, depsipeptides have lower rotational barriers for cis-trans isomerization and therefore t
Research
8,363 papers- FK228 (depsipeptide): a HDAC inhibitor with pleiotropic antitumor activities.Cancer chemotherapy and pharmacology · 2006
- Depsipeptide (FK228) as a novel histone deacetylase inhibitor: mechanism of action and anticancer activity.Mini reviews in medicinal chemistry · 2007
- Duvelisib plus romidepsin in relapsed/refractory T cell lymphomas: a phase 1b/2a trial.Nature medicine · 2024
- Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma.The Journal of antibiotics · 2011
- Oral azacitidine compared with standard therapy in patients with relapsed or refractory follicular helper T-cell lymphoma (ORACLE): an open-label randomised, phase 3 study.The Lancet. Haematology · 2024
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A depsipeptide is a peptide in which one or more amide, -C(O)NHR-, linkages are replaced by the corresponding ester, -C(O)OR-. Many depsipeptides have both peptide and ester linkages. 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. 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. They are mainly produced in nature by soil and marine sediment inhabiting bacteria. thumb|400px|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.
thumb|right|222px|Romidepsin