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Gualamycin

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Category Others
Catalog number BBF-01295
CAS 161017-23-8
Molecular Weight 590.53
Molecular Formula C21H38N2O17

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Streptomyces sp. NK11687. It has acaricidal action. 250 μg/mL of Gualamycin can completely kill mites, which is sensitive and resistant to Dicofol.

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Synonyms 2-Pyrrolidinebutanoic acid, a-[[4-O-(2-amino-2-deoxy-b-D-gulopyranosyl)-a-D-galactopyranosyl]oxy]-b,g,3,4-tetrahydroxy-5-(hydroxymethyl)-, (aR,bS,gS,2S,3S,4S,5S)-(9Cl)
IUPAC Name (2R,3S,4S)-2-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3,4-dihydroxybutanoic acid
Canonical SMILES C(C1C(C(C(N1)C(C(C(C(=O)O)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)O)N)O)O)O)O)O)O)O
InChI InChI=1S/C21H38N2O17/c22-7-11(29)10(28)5(2-25)37-20(7)39-17-6(3-26)38-21(16(34)15(17)33)40-18(19(35)36)14(32)13(31)8-12(30)9(27)4(1-24)23-8/h4-18,20-21,23-34H,1-3,22H2,(H,35,36)/t4-,5+,6+,7+,8-,9-,10-,11-,12-,13-,14-,15+,16+,17-,18+,20-,21+/m0/s1
InChI Key IZZRXUHORVVNQL-LLEMLHBASA-N
Appearance White Powder
Melting Point 174 °C
Solubility Soluble in Water
1. Gualamycin, a novel acaricide produced by Streptomyces sp. NK11687. II. Structural elucidation
K Tsuchiya, S Kobayashi, T Kurokawa, T Nakagawa, N Shimada, H Nakamura, Y Iitaka, M Kitagawa, K Tatsuta J Antibiot (Tokyo). 1995 Jul;48(7):630-4. doi: 10.7164/antibiotics.48.630.
A novel acaricide, gualamycin was isolated from the culture broth of Streptomyces sp. NK11687. The structure of gualamycin was determined to be (2R,3S,4S)-2-O-[4-O-(2-amino-2-deoxy-beta-D-gulopyranosyl)-alpha-D - galactopyranosyl]-2,3,4-trihydroxy-4-[(2S,3S,4S,5S)-3,4-dihydroxy-5-hydr oxy - methylpyrrolidin-2-yl] butanoic acid by FAB-MS, 1H and 13C NMR, COSY, HMQC, HMBC, IR, X-ray crystallographic analyses and synthetic studies.
2. Gualamycin, a novel acaricide produced by Streptomyces sp. NK11687. I. Taxonomy, production, isolation, and preliminary characterization
K Tsuchiya, S Kobayashi, T Harada, T Kurokawa, T Nakagawa, N Shimada, K Kobayashi J Antibiot (Tokyo). 1995 Jul;48(7):626-9. doi: 10.7164/antibiotics.48.626.
A novel acaricide, gualamycin, was isolated from the culture broth of Streptomyces sp. NK11687. It was purified from the filtrate by column chromatographies. Gualamycin showed 100% acaricidal activity at 250 micrograms/ml against sensitive and resistant mites to Dicofol.

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