Wikipedia

Actaplanin

Actaplanin is a complex of broad-spectrum antibiotics made by Actinoplanes bacteria.[1][2] Research carried out by a group in Eli Lilly and Co. in 1984 identified several actaplanins using high-performance liquid chromatography.[3][4][5] Actaplanins A, B1, B2, B3, C1 and G were shown to be composed of the same peptide core, an amino sugar, and varying amounts of glucose, mannose, and rhamnose.[6]

Actaplanin
Names
Other names
Antibiotic A 4696, Kamoran
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C90H101ClN8O40/c1-29-47-18-35(19-48(29)132-88-75(116)71(112)67(108)54(26-101)135-88)61-83(122)97-62-36-20-51(129-38-9-4-31(5-10-38)14-43(80(119)95-61)94-81(120)59(93)32-6-12-45(105)49(17-32)131-47)79(139-90-77(118)73(114)69(110)56(137-90)28-127-87-74(115)70(111)66(107)53(25-100)134-87)52(21-36)130-46-13-8-34(16-41(46)91)78(138-57-24-42(92)65(106)30(2)128-57)64-85(124)98-63(86(125)126-3)40-22-37(103)23-50(133-89-76(117)72(113)68(109)55(27-102)136-89)58(40)39-15-33(7-11-44(39)104)60(82(121)99-64)96-84(62)123/h4-13,15-23,30,42-43,53-57,59-78,87-90,100-118H,14,24-28,92-93H2,1-3H3,(H,94,120)(H,95,119)(H,96,123)(H,97,122)(H,98,124)(H,99,121)
    Key: PFEBYWJUETVBLJ-UHFFFAOYSA-N
  • CC1C(C(CC(O1)OC2C3C(=O)NC(C4=C(C(=CC(=C4)O)OC5C(C(C(C(O5)CO)O)O)O)C6=C(C=CC(=C6)C(C(=O)N3)NC(=O)C7C8=CC(=C(C(=C8)OC9=C(C=C2C=C9)Cl)OC1C(C(C(C(O1)COC1C(C(C(C(O1)CO)O)O)O)O)O)O)OC1=CC=C(CC2C(=O)NC(C3=CC(=C(C(=C3)OC3C(C(C(C(O3)CO)O)O)O)C)OC3=C(C=CC(=C3)C(C(=O)N2)N)O)C(=O)N7)C=C1)O)C(=O)OC)N)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

See also

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  • Ristocetin (contains the same amino sugar as in actaplanin)

References

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  1. ^ Debono, Manuel; Merkel, Kurt E.; Molloy, R. Michael; Barnhart, Mitchell; Presti, Eugene; Hunt, Ann H.; Hamill, Robert L. (1984). "Actaplanin, new glycopeptide antibiotics produced by Actinoplanes missouriensis. The isolation and preliminary chemical characterization of actaplanin". The Journal of Antibiotics. 37 (2): 85–95. doi:10.7164/antibiotics.37.85. PMID 6706856.
  2. ^ Huber, Floyd M.; Pieper, Richard L.; Tietz, Anthony J. (January 1987). "Characterization of the process for the biosynthesis of the actaplanin complex by Actinoplanes missouriensis". Journal of Fermentation Technology. 65 (1): 85–89. doi:10.1016/0385-6380(87)90069-0.
  3. ^ Debono, Manuel; Merkel, Kurt E.; Molloy, R. Michael; Barnhart, Mitchell; Presti, Eugene; Hunt, Ann H.; Hamill, Robert L. (1984). "Actaplanin, new glycopeptide antibiotics produced by Actinoplanes missouriensis. The isolation and preliminary chemical characterization of actaplanin". The Journal of Antibiotics. 37 (2): 85–95. doi:10.7164/antibiotics.37.85. PMID 6706856. Retrieved 25 December 2014.
  4. ^ US 4115552, Robert L Hamill & Donald C Delong, "Factor A and B of antibiotic A-4696", published 19 Sep 1978, assigned to Eli Lilly And Company 
  5. ^ US 4322406, Manuel Debono; Robert E. Weeks & Herald J. Cole, "Antibiotic A-4696 factors B1, B2, B3, C1a, C3 and E1", published 30 Mar 1982, assigned to Eli Lilly And Company 
  6. ^ Hunt, Ann H.; Elzey, Thomas K.; Merkel, Kurt E.; Debono, Manuel (February 1984). "Structures of the actaplanins". The Journal of Organic Chemistry. 49 (4): 641–645. doi:10.1021/jo00178a012.
 

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