Boholmycin

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Category Antibiotics
Catalog number BBF-00162
CAS 117192-99-1
Molecular Weight 764.68
Molecular Formula C27H48N4O21
Purity >98%

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Description

Boholmycin is an amino glycoside antibiotic produced by Streptomyces hygrosspicus H617-25. Its antibacterial activity is weak, but its antibacterial spectrum is broad, and it also has an effect on aminoglycosine-resistant bacteria.

Specification

Synonyms D-scyllo-Inositol, O-3-amino-3-deoxy-alpha-D-mannopyranosyl-(1-3)-O-(O-heptopyranosyl-(1-4)-2-deoxy-2-(methylamino)-alpha-D-xylopyranosyl-(1-1))-, 4,6-dicarbamate
Storage Store at -20°C
IUPAC Name [4-[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-carbamoyloxy-2-[5-[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-3-(methylamino)oxan-2-yl]oxy-3,6-dihydroxycyclohexyl] carbamate
Canonical SMILES CNC1C(C(COC1OC2C(C(C(C(C2OC(=O)N)O)OC(=O)N)OC3C(C(C(C(O3)CO)O)N)O)O)OC4C(C(C(C(O4)C(CO)O)O)O)O)O
InChI InChI=1S/C27H48N4O21/c1-31-9-11(36)7(47-25-15(40)13(38)14(39)18(48-25)5(34)2-32)4-45-23(9)49-19-16(41)20(22(52-27(30)44)17(42)21(19)51-26(29)43)50-24-12(37)8(28)10(35)6(3-33)46-24/h5-25,31-42H,2-4,28H2,1H3,(H2,29,43)(H2,30,44)
InChI Key JPGBWUBDJIISRF-UHFFFAOYSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum bacteria
Boiling Point 1171.4°C at 760 mmHg
Melting Point 214-219°C(dec.)
Density 1.75 g/cm3
Solubility Soluble in DMSO

Reference Reading

1. Boholmycin, a new aminoglycoside antibiotic. I. Production, isolation and properties
K Saitoh, M Tsunakawa, K Tomita, T Miyaki, M Konishi, H Kawaguchi J Antibiot (Tokyo). 1988 Jul;41(7):855-61. doi: 10.7164/antibiotics.41.855.
A novel aminoglycoside antibiotic, boholmycin, was produced by Streptomyces hygroscopicus H617-25 isolated from a soil sample collected in Bohol Island, the Philippines. It has a pseudotetrasaccharide structure composed of a heptose, two aminosugars and dicarbamoyl-scyllo-inositol. Intrinsic antibacterial activity of boholmycin is weak but it exhibits broad spectrum activity against Gram-positive and Gram-negative bacteria including aminoglycoside-resistant strains. Boholmycin is non-toxic in mice at 1,000 mg/kg intravenously.

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