Neoviridogrisein II
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| Category | Antibiotics |
| Catalog number | BBF-02121 |
| CAS | |
| Molecular Weight | 863.01 |
| Molecular Formula | C44H62N8O10 |
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Description
It is produced by the strain of Str. griseoviridus P8648. Neoviridogrisein II has been used to resist gram-positive bacteria and mycoplasma.
Specification
| Synonyms | 3-Phenyl-4,6,10,13,22-pentamethyl-9-(1,2-dimethylpropyl)-18-(2-methylpropyl)-21-[[(3-hydroxy-2-pyridyl)carbonyl]amino]-15,16-propano-1-oxa-4,7,10,13,16,19-hexaazacyclodocosane-2,5,8,11,14,17,20-heptone; neoviridogrisein ii |
| IUPAC Name | 3-hydroxy-N-[7,11,13,17,20-pentamethyl-16-(3-methylbutan-2-yl)-3-(2-methylpropyl)-2,5,9,12,15,18,21-heptaoxo-10-phenyl-8-oxa-1,4,11,14,17,20-hexazabicyclo[20.3.0]pentacosan-6-yl]pyridine-2-carboxamide |
| Canonical SMILES | CC1C(C(=O)NC(C(=O)N2CCCC2C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)O1)C3=CC=CC=C3)C)C)C(C)C(C)C)C)C)CC(C)C)NC(=O)C4=C(C=CC=N4)O |
| InChI | InChI=1S/C44H62N8O10/c1-24(2)22-30-42(59)52-21-15-18-31(52)43(60)49(8)23-33(54)50(9)36(26(5)25(3)4)40(57)46-27(6)41(58)51(10)37(29-16-12-11-13-17-29)44(61)62-28(7)34(38(55)47-30)48-39(56)35-32(53)19-14-20-45-35/h11-14,16-17,19-20,24-28,30-31,34,36-37,53H,15,18,21-23H2,1-10H3,(H,46,57)(H,47,55)(H,48,56) |
| InChI Key | XMKLKZFSQXZUQU-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycoplasma |
| Melting Point | 145°C |
Reference Reading
1. Controlled biosynthesis of neoviridogriseins, new homologues of viridogrisein II. Production, biological properties and structure of neoviridogrisein II
Y Okumura, T Takei, M Sakamoto, T Ishikura, Y Fukagawa J Antibiot (Tokyo). 1979 Jun;32(6):584-92. doi: 10.7164/antibiotics.32.584.
Our isolate of Streptomyces griseoviridus, which produced three minor factors in addition to viridogrisein and griseoviridus, which produced three minor factors in addition to viridogrisein and griseoviridin, was more sensitive to the addition of L-proline than the type culture of Streptomyces griseoviridus (NRRL2427). Yield improvement of these minor factors was attempted by the so-called controlled biosynthesis with L-proline. Addition of L-proline increased the production of neoviridogrisein II in which allo-hydroxy-D-proline in viridogrisein was replaced by D-proline.
2. Controlled biosynthesis of neoviridogriseins, new homologues of viridogrisein. IV. In vitro synergism between neoviridogrisein II and the antibiotics of the mikamycin A group
Y Okumura, M Sakamoto, T Takei, T Ishikura, Y Fukagawa J Antibiot (Tokyo). 1979 Nov;32(11):1130-6. doi: 10.7164/antibiotics.32.1130.
Neoviridogrisein II is a homologue of viridogrisein in which the hydroxyproline residue is replaced by proline. Neoviridogrisein II proved to be more active than the parent antibiotic against Gram-positive bacteria and Mycoplasma species. When neoviridogrisein II or viridogrisein was combined with griseoviridin, a non-peptidyl macrocyclic lactone, synergism was observed: maximum synergistic effect was observed for a combination ratio that depended on the test bacterium used. Neoviridogrisein II also exerted synergism when combined with mikamycin A and A-2315A.
3. Probing the substrate specificity of an enzyme catalyzing inactivation of streptogramin B antibiotics using LC-MS and LC-MS/MS
K P Bateman, P Thibault, K Yang, R L White, L C Vining J Mass Spectrom. 1997 Oct;32(10):1057-63. doi: 10.1002/(SICI)1096-9888(199711)32:103.0.CO;2-D.
LC-MS and LC-MS/MS analyses indicated that an enzyme responsible for inactivating the antibiotic etamycin is specific for streptogramins and acts on both type B-I and B-II streptogramin subgroups. No enzymatic activity was detected for other cyclodepsipeptides such as surfactins and viscosin. It was demonstrated using analogs of etamycin that the picolinyl moiety is essential to obtain enzyme-generated ring-opened compounds. Because the picolinyl moiety is also essential for the biological activity of streptogramins, it is proposed that this residue is a distinctive topographic feature in the binding of this group of antibiotics to enzyme active sites.
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
