Thiopeptide






Chemical structure of thiostrepton, a thiopeptide


Thiopeptides (thiazolyl peptides) are a class of peptide antibiotics produced by bacteria. They have antibiotic activity against Gram-positive bacteria, but little or no activity against Gram-negative bacteria.[1] Many of the members of this class show activity against methicillin-resistant Staphylococcus aureus (MRSA) and are therefore subjects of research interest.


There are over 100 members of this class known.[2]



Chemical structure


Thiopeptides are sulfur-rich macrocyclic peptides containing highly-modified amino acids. They are characterized by a nitrogen-containing six-membered ring (such as piperidine, dehydropiperidine, or pyridine) substituted with multiple thiazole rings and dehydroamino acids.[3] A macrocylic ring serves as a scaffold for a tail that also incorporates modified amino acids often with azole rings, such as thiazoles, oxazoles, and thiazolines which are derived from serine, threonine, and cysteine residues.[3]



Examples


Examples of thiopeptides include thiostrepton, cyclothiazomycin, nosiheptide, and lactocillin.



References





  1. ^ Bagley, Mark C.; Dale, James W.; Merritt, Eleanor A.; Xiong, Xin (2005). "Thiopeptide Antibiotics". Chemical Reviews. 105 (2): 685. doi:10.1021/cr0300441. PMID 15700961..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  2. ^ "THIOBASE: a Database of Thiopeptides Featured in Genetics and Chemistry".


  3. ^ ab Just-Baringo, X; Albericio, F; Álvarez, M (2014). "Thiopeptide Antibiotics: Retrospective and Recent Advances". Marine Drugs. 12 (1): 317–351. doi:10.3390/md12010317. PMC 3917276.









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