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G1424

Sigma-Aldrich

Globomycin from Streptomyces hagronensis

Synonym(s):

Globomycin, Glycine, N-(N-(N-(N-(N-(3-hydroxy-2-methyl-1-oxononyl)-N-methylleucyl)-L-alloisoleucyl)-L-seryl)-L-allothreonyl)-, rho-lactone, SF 1902

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About This Item

Empirical Formula (Hill Notation):
C32H57N5O9
CAS Number:
Molecular Weight:
655.82
MDL number:
UNSPSC Code:
51102829
NACRES:
NA.85

biological source

Streptomyces hagronensis

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: 1 mg/mL

antibiotic activity spectrum

Gram-negative bacteria

Mode of action

enzyme | inhibits

storage temp.

−20°C
−20°C

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)

InChI key

VFGBXFZXJAWPOE-UHFFFAOYSA-N

General description

Globomycin is a cyclic peptide antibiotic, which inhibits the growth of enteric Gram-negative bacteria through cell wall synthesis inhibition.

Application


  • Globomycin, a new peptide antibiotic with spheroplast-forming activity. I. Taxonomy of producing organisms and fermentation.: This study explores the taxonomy of the producing organisms of Globomycin and details the fermentation processes involved. This antibiotic shows spheroplast-forming activity, indicating its potential application in targeting bacterial cell wall synthesis (Inukai et al., 1978).

Biochem/physiol Actions

Globomycin was found to inhibit LspA, a lipoprotein signal peptidase. It eliminates the maturation of pro-lipoproteins by inhibition of the enzyme that converts pro-lipoprotein to lipoprotein, acting as a substrate analog of the signal sequence in the outer membrane of Gram-negative bacteria.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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E Deák et al.
Microbiology (Reading, England), 144 ( Pt 8), 2169-2177 (1998-08-28)
A new type of beta-lactamase has been isolated and characterized in Streptomyces griseus NRRL B-2682. The enzyme has membrane-bound and extracellular forms. Biochemical characterization of some of the properties of the enzyme showed that it belongs to the class A
S Daefler et al.
Molecular microbiology, 28(6), 1367-1380 (1998-07-29)
The secretion of pathogenicity factors by Salmonella typhimurium is mediated by a type III secretion system that includes an outer membrane protein of the secretin family. Related secretins are also required for f1 phage assembly and type II secretion. When
Toshihiro Kiho et al.
Bioorganic & medicinal chemistry letters, 13(14), 2315-2318 (2003-06-26)
Globomycin, a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. One of the analogues showed a more potent activity against Gram-negative bacteria than
Yao Xiao et al.
Antimicrobial agents and chemotherapy, 56(4), 2014-2021 (2012-01-11)
Antibiotic TA is a macrocyclic secondary metabolite produced by myxobacteria that has broad-spectrum bactericidal activity. The structure of TA is unique, and its molecular target is unknown. Here, we sought to elucidate TA's mode of action (MOA) through two parallel
Y Paitan et al.
Journal of bacteriology, 181(18), 5644-5651 (1999-09-11)
Myxococcus xanthus is a gram-negative soil bacterium that produces the polyketide antibiotic TA. In this study, we describe the analysis of an M. xanthus gene which encodes a homologue of the prolipoprotein signal peptidase II (SPase II; lsp). Overexpression of

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