Globomycin

Globomycin is a lipopeptide antibiotic and a signal peptidase II (LspA) inhibitor. Globomycin inhibits processing of the prolipoprotein by binding irreversibly to the peptidase. Globomycin has toxic for the mollicute Spiroplasma melliferum with a MIC in the range 6.25-12.5 μM.

Product information

CAS Number: 67076-74-8

Molecular Weight: 655.82

Formula: C32H57N5O9

Chemical Name: 12-butan-2-yl-19-hexyl-6-(1-hydroxyethyl)-9-(hydroxymethyl)-16, 18-dimethyl-15-(2-methylpropyl)-1-oxa-4, 7, 10, 13, 16-pentazacyclononadecane-2, 5, 8, 11, 14, 17-hexone

Smiles: CC(C)CC1C(=O)NC(C(C)CC)C(=O)NC(CO)C(=O)NC(C(C)O)C(=O)NCC(=O)OC(CCCCCC)C(C)C(=O)N1C

InChiKey: VFGBXFZXJAWPOE-UHFFFAOYSA-N

InChi: InChI=1S/C32H57N5O9/c1-9-11-12-13-14-24-20(6)32(45)37(8)23(15-18(3)4)29(42)35-26(19(5)10-2)31(44)34-22(17-38)28(41)36-27(21(7)39)30(43)33-16-25(40)46-24/h18-24,26-27,38-39H,9-17H2,1-8H3,(H,33,43)(H,34,44)(H,35,42)(H,36,41)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Globomycin is capable of inhibiting the growth of S. melliferum. The MICs are 6.25 µM (4.1 µg/mL) for strain BC3 and 12.5 µM (8.2 µg/mL) for strain B88. Globomycin can interfere with the processing of bacterial lipoproteins by inhibition of signal peptidase II in gracilicutes (Gram-negative eubacteria) and firmicutes (Gram-positive eubacteria). In B. diminuta DS010 cells, in the Globomycin-treated cultures most of the organophosphate hydrolase (OPH) accumulates in the cytoplasmic fraction in an unprocessed form. This is in contrast with the untreated cells where very little precursor was detectable. Moreover, there is substantially less mature OPH detectable in the membrane fraction following Globomycin treatment. The OPH signal peptide contains an invariant cysteine residue at the junction of the signal peptidase (Spase) cleavage site along with a well conserved lipobox motif. Substitution of the conserved lipobox cysteine to serine resulted in release of OPH into the periplasm, confirming that OPH is a lipoprotein.

References:

1. Beven L, et al. Inhibition of spiralin processing by the lipopeptide antibiotic globomycin. Curr Microbiol. 1996 Nov;33(5):317-22.
2. Parthasarathy S, et al. Organophosphate Hydrolase Is a Lipoprotein and Interacts with Pi-specific Transport System to Facilitate Growth of Brevundimonas diminuta Using OP Insecticide as Source of Phosphate. J Biol Chem. 2016 Apr 1;291(14):7774-85.

Products are for research use only. Not for human use.