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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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1 MG
$591.56

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1 MG
$591.56

About This Item

Empirical Formula (Hill Notation):
C32H57N5O9
CAS Number:
67076-74-8
Molecular Weight:
655.82
MDL number:
MFCD32661892
UNSPSC Code:
51102829
NACRES:
NA.85

$591.56

List Price$643.00Save 8%
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order

biological source

Streptomyces hagronensis

Quality Level

200

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

SMILES string

N1(C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)OC(C(C1=O)C)CCCCCC)C(O)C)CO)C(CC)C)CC(C)C)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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
14190114
099M4057V
108M4057V
14180420
067M4158V

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Isabelle Leduc et al.
Infection and immunity, 72(6), 3418-3428 (2004-05-25)
Haemophilus ducreyi, the causative agent of chancroid, is highly resistant to the complement-mediated bactericidal activity of normal human serum (NHS). Previously, we identified DsrA (for ducreyi serum resistance A), a major factor required for expression of the serum resistance phenotype
Suneeta Khandavilli et al.
Molecular microbiology, 67(3), 541-557 (2007-12-19)
Cell surface lipoproteins are important for the full virulence of several bacterial pathogens, including Streptococcus pneumoniae. Processing of prolipoproteins seems to be conserved among different bacterial species, and requires type II signal peptidase (Lsp) mediated cleavage of the N-terminal signal
D A Haake et al.
Infection and immunity, 66(4), 1579-1587 (1998-04-07)
We report the cloning of the gene encoding a 36-kDa leptospiral outer membrane lipoprotein, designated LipL36. We obtained the N-terminal amino acid sequence of a staphylococcal V8 proteolytic-digest fragment in order to design an oligonucleotide probe. A Lambda-Zap II library
Francisco Sarabia et al.
The Journal of organic chemistry, 76(7), 2132-2144 (2011-03-04)
The syntheses of the natural lipocyclodepsipeptide-type antibiotics globomycin and SF-1902 A(5) are reported, utilizing solid phase technology for the construction of the peptidic fragment and a new asymmetric methodology of epoxidation for the preparation of the lipidic chain. The linkage
Mikio Shoji et al.
Molecular microbiology, 52(5), 1513-1525 (2004-05-29)
Bacterial cell surface filaments play significant roles in adherence to and invasion of host cells. They are generated by the chaperone/usher pathway system (class I fimbriae), the type II secretion system (type IV pili) and the nucleation-dependent polymerization system (Curli
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