Английская Википедия:Depsipeptide
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]
Depsipeptide natural products
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]
Etamycin was shown in preliminary data in 2010 to have potent activity against MRSA in a mouse model.[8] Several depsipeptides from Streptomyces exhibit antimicrobial activity.[9][10] These form a new, potential class of antibiotics known as acyldepsipeptides (ADEPs). ADEPs target and activate the casein lytic protease (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
- ↑ Шаблон:GoldBookRef
- ↑ 2,0 2,1 2,2 Шаблон:Cite journal
- ↑ 3,0 3,1 Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ K. H. Michel, R. E. Kastner (Eli Lilly and Company), US 4492650, 1985 [Chem. Abstr. 1985, 102, 130459]
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Citation
Further reading
- papuamide Шаблон:Cite journal
- neamphamide A Шаблон:Cite journal
- callipeltin A Шаблон:Cite journal
- mirabamides A-D Шаблон:Cite journal; Шаблон:Cite journal