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.
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "depsipeptides". doi:10.1351/goldbook.D01604
^ abcAvan, Ilker; Tala, Srinivasa R.; Steel, Peter J.; Katritzky, Alan R. (17 June 2011). "Benzotriazole-Mediated Syntheses of Depsipeptides and Oligoesters". The Journal of Organic Chemistry. 76 (12): 4884–4893. doi:10.1021/jo200174j. PMID 21452874.
^ abAvan, Ilker; Hall, C. Dennis; Katritzky, Alan R. (2014). "Peptidomimetics via modifications of amino acids and peptide bonds". Chemical Society Reviews. 43 (10): 3575–3594. doi:10.1039/C3CS60384A. PMID 24626261.
^Yasumasa Hamada; Takayuki Shioiri (2005). "Recent Progress of the Synthetic Studies of Biologically Active Marine Cyclic Peptides and Depsipeptides". Chem. Rev. 105 (12): 4441–4482. doi:10.1021/cr0406312. PMID 16351050.
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-. Many depsipeptides have...
development of uveal melanoma and its pharmacological inhibition (cyclic depsipeptide FR900359 inhibitor), decreases tumor growth in preclinical trials. The...
cereulide, this cyclic ester (or lactone) linkage makes cereulide a depsipeptide. CesA is a 387 kDa heterodimer protein composed of CesA1 and CesA2 modules...
deacetylases, thus inducing apoptosis. It is sometimes referred to as depsipeptide, after the class of molecules to which it belongs. Romidepsin is branded...
Auristatin E) CD30 and Microtubules 9/19 Cancer Plitidepsin Aplidin Tunicate Depsipeptide Rac1 and JNK Activation 1/7 Cancer Phase II DMXBA (GTS-21) N/A Worm Alkaloid...
properties useful in developing chemotherapy. They are members of the depsipeptide family. Cryptophycins were originally discovered in 1990 in cyanobacteria...
composed of two or more monocyclic aromatic units linked by an ester group Depsipeptide, a type of ester that is a peptide in which one or more of its amide...
spectrum of action to erythromycin. Pristinamycin IA (streptogramin B) is a depsipeptide. PI and PII are coproduced by S. pristinaespiralis in a ratio of 30:70...
920. Ciufolini, M.A.; Swaminathan, S. (1989). "Synthesis of a model depsipeptide segment of Luzopeptins (BBM 928), potent antitumor and antiretroviral...
was reported in 1990. Microviridins are characterized by a tricyclic depsipeptide structure resulting from the enzymatic activity of two dedicated ATP-grasp...
Ambobactin is an depsipeptide antibiotic with the molecular formula C59H77N13O19. Ambobactin is produced by the bacterium Streptomyces ambofaciens. "Ambobactin"...
group of another residue, as in microcystin and bacitracin. Cyclic depsipeptides, such as aureobasidin A and HUN-7293, have at least one lactone (ester)...
Lyngbyastatins 1 and 3 are cytotoxic cyclic depsipeptides that possess antiproliferative activity against human cancer cell lines. These compounds, first...
Dactinomycin, also known as actinomycin D, is a chemotherapy medication used to treat a number of types of cancer. This includes Wilms tumor, rhabdomyosarcoma...
Kettapeptin is a depsipeptide antibiotic isolated from Streptomyces. It is effective against gram positive bacteria, as well as the fungi Candida albicans...
Mortensen OV, Osei-Owusu P (2019). "Anti-hypertensive mechanisms of cyclic depsipeptide inhibitor ligands for G(q/11) class G proteins". Pharmacol Res. 141:...
Daptomycin, sold under the brand name Cubicin among others, is a lipopeptide antibiotic used in the treatment of systemic and life-threatening infections...
substituted side chains, macrocyclic lactams and macrocyclic peptide or depsipeptide antibiotics like the katanosins. Lysobacter spp. have been described...
as trichostatin A, cyclic tetrapeptides (such as trapoxin B, and the depsipeptides, such as romidepsin benzamides, electrophilic ketones, and the aliphatic...
Keanumycins are a group of chemical compounds isolated from bacteria in the genus Pseudomonas. They are classified as nonribosomal lipopeptides and they...
Aurantimycin A is a depsipeptide antibiotic with the molecular formula C38H64N8O14. Aurantimycin A is produced by the bacterium Streptomyces aurantiacus...
Thiocoraline is a microbial natural product of the depsipeptide class. Thiocoraline was isolated from the mycelium cake of a marine actinomycete strain...
Didemnins are cyclic depsipeptide compounds isolated from a tunicate (ascidian, or sea-squirt) of the genus Trididemnum (family of Didemnidæ) that were...
Beauvericin is a depsipeptide with antibiotic and insecticidal effects belonging to the enniatin family. It was isolated from the fungus Beauveria bassiana...
Richard; Bode, Helge B (11 April 2012). "Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium...
Valinomycin is a naturally occurring dodecadepsipeptide used in the transport of potassium and as an antibiotic. Valinomycin is obtained from the cells...