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RS-22C

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Category Antibiotics
Catalog number BBF-03391
CAS
Molecular Weight 1082.4
Molecular Formula C56H95N3O17

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Fermentation Lab

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2 Preparative purification labs

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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

RS-22C is a macrolide antibiotic produced by Streptomyces violaceusniger. It is active against gram-positive, gram-negative bacteria, yeast and filamentous fungi.

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Synonyms RS-22 C
IUPAC Name 3-[[(10E,12E,18E,20E)-15-[(E)-10-[(N,N'-dimethylcarbamimidoyl)amino]dec-6-en-2-yl]-5,7,9,23,25,27,31,33,34,35-decahydroxy-10,14,22,26,30-pentamethyl-17-oxo-16,37-dioxabicyclo[31.3.1]heptatriaconta-10,12,18,20-tetraen-3-yl]oxy]-3-oxopropanoic acid
Canonical SMILES CC1CCC(C(C(CC(C(C=CC=CC(=O)OC(C(C=CC=C(C(CC(CC(CC(CC2CC(C(C(O2)(CC1O)O)O)O)OC(=O)CC(=O)O)O)O)O)C)C)C(C)CCCC=CCCCNC(=NC)NC)C)O)O)C)O
InChI InChI=1S/C56H95N3O17/c1-34-18-14-15-22-51(70)75-53(37(4)19-13-11-9-10-12-16-25-59-55(57-7)58-8)38(5)21-17-20-35(2)45(63)28-41(61)26-40(60)27-42(74-52(71)32-50(68)69)29-43-30-48(66)54(72)56(73,76-43)33-49(67)36(3)23-24-44(62)39(6)47(65)31-46(34)64/h9-10,14-15,17-18,20-22,34,36-49,53-54,60-67,72-73H,11-13,16,19,23-33H2,1-8H3,(H,68,69)(H2,57,58,59)/b10-9+,18-14+,21-17+,22-15+,35-20+
InChI Key QZHGHZHNPQLENX-IPSANITBSA-N
Appearance Colorless Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; yeast; fungi
Melting Point 129-132°C
1. RS-22A, B and C: new macrolide antibiotics from Streptomyces violaceusniger. I. Taxonomy, fermentation, isolation and biological activities
M Ubukata, N Shiraishi, K Kobinata, T Kudo, I Yamaguchi, H Osada, Y C Shen, K Isono J Antibiot (Tokyo). 1995 Apr;48(4):289-92. doi: 10.7164/antibiotics.48.289.
Three novel 36-membered macrolide antibiotics, RS-22A, B and C produced by Streptomyces violaceusniger have been isolated. These antibiotics were purified from an acetone extract of the mycelia followed by butanol extraction, centrifugal partition chromatography and HPLC. RS-22A, B, C showed antimicrobial activity against fungi and Gram-positive bacteria.
2. RS-22A, B and C: new macrolide antibiotics from Streptomyces violaceusniger. II. Physico-chemical properties and structure elucidation
M Ubukata, T Morita, H Osada J Antibiot (Tokyo). 1995 Apr;48(4):293-9. doi: 10.7164/antibiotics.48.293.
RS-22A, B and C are novel 36-membered macrolide antibiotics produced by Streptomyces violaceusniger. The structures of these antibiotics were unambiguously determined by 1D and 2D NMR and tandem-mass analysis of the oxidative derivative of RS-22C.
3. N'-methylniphimycin, a novel minor congener of niphimycin from Streptomyces spec. 57-13
V Ivanova, R Schlegel, K Dornberger J Basic Microbiol. 1998;38(5-6):415-9. doi: 10.1002/(sici)1521-4028(199811)38:5/63.0.co;2-z.
A novel natural niphimycin analog, N'-methylniphimycin was isolated from the culture broth of the Streptomyces spec. 57-13. The chemical constitution was elucidated from the physico-chemical properties, NMR techniques and mass spectrometry to be a 36-membered macrolide related to azalomycin F5a, shurimycin B and RS-22C. N'-methylniphimycin displayed moderate activity against some yeasts and filamentous fungi.

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