Siamycin I

Siamycin I (BMY-29304), a 21-residue tricyclic peptide, is a secondary metabolite in actinomycetes. Siamycin I is a HIV fusion inhibitor with ED50s of 0.05 to 5.7 μM for acute HIV type 1 (HIV-1) and HIV-2 infections. Siamycin I inhibits the gelatinase and gelatinase biosynthesis-activating pheromone (GBAP) signaling via the FsrC-FsrA two-component regulatory system in a noncompetitive manner. Siamycin I suppresses the expression of both fsrBDC and gelE-sprE transcripts. Siamycin I, a lasso peptide, interacts with lipid II and inhibits cell wall biosynthesis. Siamycin I, an antibiotic, has the potential for enterococcal infections research[1][2][3][4].

Product Specifications

CAS Number

[164802-68-0]

Product Name Alternative

BMY-29304

UNSPSC

12352209

Target

Antibiotic; HIV

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-anti-virus

Field of Research

Infection; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/siamycin-i.html

Solubility

10 mM in DMSO

Smiles

O=C([C@H]1NC([C@@H](NC([C@](NC([C@@H](NC([C@@H](NC(CNC([C@](N2)([H])CSSC[C@]3([H])NC(C[C@](C(NC(C(N[C@H](C(NCC2=O)=O)C)=O)CC4=CC=CC=C4)=O)([H])NC([C@H](CC(N)=O)NC([C@](NC([C@@H](NC(CNC([C@@H](NC(CNC([C@H](CC(C)C)NC3=O)=O)=O)C(C)C)=O)=O)CO)=O)([H])CSSC1)=O)=O)=O)=O)=O)CC5=CC=C(O)C=C5)=O)C)=O)([H])[C@@H](C)CC)=O)C(C)C)=O)N[C@@H](CC6=CC=CC=C6)C(N[C@H](C(O)=O)CC7=CNC8=C7C=CC=C8)=O

Molecular Formula

C97H131N23O26S4

Molecular Weight

2163.48

References & Citations

[1]Pikyee Ma, et al. Anti-HIV siamycin I directly inhibits autophosphorylation activity of the bacterial FsrC quorum sensor and other ATP-dependent enzyme activities. FEBS Lett. 2011 Sep 2;585 (17) :2660-4.|[2]Stephanie Tan, et al. The Lasso Peptide Siamycin-I Targets Lipid II at the Gram-Positive Cell Surface. ACS Chem Biol. 2019 May 17;14 (5) :966-974.|[3]Jiro Nakayama, et al. Siamycin attenuates fsr quorum sensing mediated by a gelatinase biosynthesis-activating pheromone in Enterococcus faecalis. J Bacteriol. 2007 Feb;189 (4) :1358-65.|[4]M Tsunakawa, et al. Siamycins I and II, new anti-HIV peptides: I. Fermentation, isolation, biological activity and initial characterization. J Antibiot (Tokyo) . 1995 May;48 (5) :433-4.