Lugdunin

Lugdunin
Names
	IUPAC name (1R,4R,7S,10R,13S,16R,19S)-7-(1H-Indol-3-ylmethyl)-10-isobutyl-4,13,16,19-tetraisopropyl-21-thia-3,6,9,12,15,18,23-heptaazabicyclo[18.2.1]tricosane-2,5,8,11,14,17-hexone
Identifiers
CAS Number	1989698-37-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:133127 ;
ChemSpider	57427231;
PubChem CID	121596231;
	InChI InChI=1S/C40H62N8O6S/c1-19(2)15-27-35(50)45-31(21(5)6)38(53)47-32(22(7)8)39(54)48-33(23(9)10)40-44-29(18-55-40)36(51)46-30(20(3)4)37(52)43-28(34(49)42-27)16-24-17-41-26-14-12-11-13-25(24)26/h11-14,17,19-23,27-33,40-41,44H,15-16,18H2,1-10H3,(H,42,49)(H,43,52)(H,45,50)(H,46,51)(H,47,53)(H,48,54)/t27-,28+,29+,30-,31+,32-,33+,40?/m1/s1 Key: QZNGYMKAHFFKCJ-ZBQZSICZSA-N; InChI=1/C40H62N8O6S/c1-19(2)15-27-35(50)45-31(21(5)6)38(53)47-32(22(7)8)39(54)48-33(23(9)10)40-44-29(18-55-40)36(51)46-30(20(3)4)37(52)43-28(34(49)42-27)16-24-17-41-26-14-12-11-13-25(24)26/h11-14,17,19-23,27-33,40-41,44H,15-16,18H2,1-10H3,(H,42,49)(H,43,52)(H,45,50)(H,46,51)(H,47,53)(H,48,54)/t27-,28+,29+,30-,31+,32-,33+,40?/m1/s1 Key: QZNGYMKAHFFKCJ-ZBQZSICZBY;
	SMILES CC(C)C[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C2N[C@@H](CS2)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)Cc3c[nH]c4c3cccc4)C(C)C)C(C)C)C(C)C)C(C)C;
Properties
Chemical formula	C40H62N8O6S
Molar mass	783.05 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Lugdunin is an investigational antibiotic, classified as a thiazolidine-containing cyclic peptide. It was isolated in 2016 after Staphylococcus lugdunensis was identified as the species of bacteria from the human nose that suppressed growth of species of disease-causing bacteria in that part of the human microbiome.^[1]^[2]^[3]

Lugdunin is a non-ribosomally synthesized cyclic peptide that inhibits growth of Staphylococcus aureus strains. The lugdunin genes are located on a 30-kbp operon. The genes lugA, lugB, lugC, and lugD encode four non-ribosomal peptide synthases, which are preceded by a putative regulator gene lugR.^[4]

Gene	locustag	protein size/aa	Genbank protein entry	RefSeq protein entry
lugR	SLUG_RS03935	196	CCB53263.1	WP_002460032.1
lugA	SLUG_RS03940	2374	CCB53264.1	WP_002478842.1
	SLUG_RS03945	124	CCB53265.1	WP_002460029.1
lugB	SLUG_RS03950	1230	CCB53266.1	WP_014533237.1
lugC	SLUG_RS03955	2937	CCB53267.1	WP_002478844.1
lugT	SLUG_RS03960	228	CCB53268.1	WP_002460022.1
lugD	SLUG_RS03965	579	CCB53269.1	WP_002478846.1

References[]

^ Gallagher, James (2016-07-27). "Antibiotic resistance: 'Snot wars' study heralds new class of drugs". BBC News. Retrieved 2016-07-27.
^ Zipperer, Alexander; Konnerth, Martin C.; Laux, Claudia; Berscheid, Anne; Janek, Daniela; Weidenmaier, Christopher; Burian, Marc; Schilling, Nadine A.; Slavetinsky, Christoph (2016). "Human commensals producing a novel antibiotic impair pathogen colonization". Nature. 535 (7613): 511–516. Bibcode:2016Natur.535..511Z. doi:10.1038/nature18634. PMID 27466123. S2CID 205249755.
^ "Scientists find microbiotic treasure hidden in the nose". Los Angeles Times. 2016-07-27. Retrieved 2016-07-27.
^ Krismer, Bernhard; Peschel, Andreas; Grond, Stephanie; Brötz-Oesterhelt, Heike; Schittek, Birgit; Kalbacher, Hubert; Willmann, Matthias; Marschal, Matthias; Slavetinsky, Christoph; Schilling, Nadine A.; Burian, Marc; Weidenmaier, Christopher; Janek, Daniela; Berscheid, Anne; Laux, Claudia; Konnerth, Martin C.; Zipperer, Alexander (July 2016). "Extended Data Figure 1: Gene cluster of lugdunin and generation of S. lugdunensis IVK28-Xyl". Nature. 535 (7613): 511–516. Bibcode:2016Natur.535..511Z. doi:10.1038/nature18634. PMID 27466123. S2CID 205249755.

External links[]

"Press release: A potential lifesaver lies unrecognized in the human body" (PDF). www.uni-tuebingen.de. University of Tübingen. Retrieved 2016-07-28.

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[1] Gallagher, James (2016-07-27). "Antibiotic resistance: 'Snot wars' study heralds new class of drugs". BBC News. Retrieved 2016-07-27.

[2] Zipperer, Alexander; Konnerth, Martin C.; Laux, Claudia; Berscheid, Anne; Janek, Daniela; Weidenmaier, Christopher; Burian, Marc; Schilling, Nadine A.; Slavetinsky, Christoph (2016). "Human commensals producing a novel antibiotic impair pathogen colonization". Nature. 535 (7613): 511–516. Bibcode:2016Natur.535..511Z. doi:10.1038/nature18634. PMID 27466123. S2CID 205249755.

[3] "Scientists find microbiotic treasure hidden in the nose". Los Angeles Times. 2016-07-27. Retrieved 2016-07-27.

[4] Krismer, Bernhard; Peschel, Andreas; Grond, Stephanie; Brötz-Oesterhelt, Heike; Schittek, Birgit; Kalbacher, Hubert; Willmann, Matthias; Marschal, Matthias; Slavetinsky, Christoph; Schilling, Nadine A.; Burian, Marc; Weidenmaier, Christopher; Janek, Daniela; Berscheid, Anne; Laux, Claudia; Konnerth, Martin C.; Zipperer, Alexander (July 2016). "Extended Data Figure 1: Gene cluster of lugdunin and generation of S. lugdunensis IVK28-Xyl". Nature. 535 (7613): 511–516. Bibcode:2016Natur.535..511Z. doi:10.1038/nature18634. PMID 27466123. S2CID 205249755.

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