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Merck
CN

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:
67076-74-8
Molecular Weight:
655.82
MDL number:
MFCD32661892
UNSPSC Code:
51102829
NACRES:
NA.85

Key Documents

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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

Related Categories

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

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000473151
0000473151
14190114
099M4057V
108M4057V

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H Loferer et al.
Molecular microbiology, 26(1), 11-23 (1998-01-31)
Curli, an adhesive surface fibre produced by Escherichia coli and salmonellae, was proposed on the basis of genetic evidence to follow a distinct assembly pathway involving an extracellular intermediate of the fibre subunit CsgA, the polymerization of which can be
Toshihiro Kiho et al.
Drug design and discovery, 18(4), 109-116 (2004-11-24)
Globomycin (1), a 19-membered cyclic depsipeptide, exhibited an antibiotic activity against gram-negative bacteria by inhibiting signal peptidase II in the cytoplasmic membrane. Although only one conformation of 1 was observed for the crystal structure, it was revealed by 1H NMR
Henry S Gibbons et al.
Journal of bacteriology, 189(14), 5090-5100 (2007-05-15)
The SecA2 protein is part of a specialized protein export system of mycobacteria. We set out to identify proteins exported to the bacterial cell envelope by the mycobacterial SecA2 system. By comparing the protein profiles of cell wall and membrane
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
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
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