Sannamycin B

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Sannamycin B
Category Antibiotics
Catalog number BBF-02867
CAS 72503-80-1
Molecular Weight 332.44
Molecular Formula C15H32N4O4

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Description

It is an aminoglycoside antibiotic produced by the strain of Str. sannanensis sp. nov. It has only weak antibacterial activity against a few bacteria.

Specification

Synonyms Istamycin A0; Antibiotic KA 7038III; KA 7038III; L-chiro-Inositol, 4-amino-3-O-(2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-alpha-D-erythro-hexopyranosyl)-1,4,5-trideoxy-6-O-methyl-1-(methylamino)-; 4-Amino-3-O-[2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-α-D-erythro-hexopyranosyl]-1,4,5-trideoxy-6-O-methyl-1-(methylamino)-L-chiro-inositol; ara-sangivamycin
IUPAC Name (1R,2R,3S,5S,6S)-3-amino-2-[(2R,3R,6S)-3-amino-6-(methylaminomethyl)oxan-2-yl]oxy-5-methoxy-6-(methylamino)cyclohexan-1-ol
Canonical SMILES CNCC1CCC(C(O1)OC2C(CC(C(C2O)NC)OC)N)N
InChI InChI=1S/C15H32N4O4/c1-18-7-8-4-5-9(16)15(22-8)23-14-10(17)6-11(21-3)12(19-2)13(14)20/h8-15,18-20H,4-7,16-17H2,1-3H3/t8-,9+,10-,11-,12+,13+,14+,15+/m0/s1
InChI Key GKYYNFPFPFRFFN-LHPGNBRISA-N

Properties

Appearance Solid
Boiling Point 480.6°C at 760 mmHg
Density 1.17 g/cm3
Solubility Soluble in Water

Reference Reading

1. Cloning and analysis of a gene (sms13) encoding sannamycin B-glycyltransferase from Streptomyces sannanensis and its distribution among actinomycetes
T Ohta, E Hashimoto, M Hasegawa J Antibiot (Tokyo). 1992 Jul;45(7):1167-75. doi: 10.7164/antibiotics.45.1167.
A gene encoding sannamycin B-glycyltransferase (sms13) of Streptomyces sannanensis IFO 14239 was identified by cloning and complementation of S. sannanensis mutant SN13 which is blocked at the interconversion of sannamycins B and A. The cloned DNA fragment also permitted the conversion of fortimicin B to A both in S. sannanensis SN13 and Streptomyces lividans TK23. DNA sequences similar to sms13 were detected in all five producers of the fortimicin-group antibiotics, Micromonospora olivasterospora ATCC 21819 (fortimicin-producer), Micromonospora sp. strain SF-2098 ATCC 31580 (SF-2052), Dactylosporangium matsuzakiense ATCC 31570 (dactimicin), Streptomyces tenjimariensis ATCC 31603 (istamycin), and Saccharopolyspora hirsuta ATCC 20501 (sporaricin). This suggests that these genes of similar function from different genera were derived from a common ancestral gene.

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