An antibiotic complex
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Ramoplanin Complex

Item No. 28189

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
ramoplanin A1, A2, and A3 (mixture)
CAS Number
76168-82-6
Synonyms
  • A-16686
  • MDL 62198
Molecular Formula
C119H154ClN21O40 (for A2)
Formula Weight
2554.1
Purity
≥80% (Ramoplanin A2)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
234, 267 nm
SMILES
OC(C=C1)=CC=C1[C@H](C(N[C@H](CCCN)C(N[C@@]([C@H](O)C)([H])C(N[C@@H](C2=CC=C(O)C=C2)C(N[C@H](C3=CC=C(O)C=C3)C(NC([C@H](C)O)C(N[C@@H](CC4=CC=CC=C4)C(N[C@H](CCCN)C(N[C@@H](C5=CC=C(O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O[C@]7([H])[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O7)C=C5)C8=O)=O)=O)=O)=O)=O)=O)=O)=O)NC([C@@H](NC([C@@H](NC(/C=C\C=C\CCC)=O)CC(N)=O)=O)[C@@H](C(N)=O)OC([C@]([H])(C9=CC=C(O)C(Cl)=C9)NC([C@@H](C)NC([C@H](CC(C)C)NC(CNC([C@H](C%10=CC=C(O)C=C%10)NC([C@]([C@H](O)C)([H])N8)=O)=O)=O)=O)=O)=O)=O.OC(C=C%11)=CC=C%11[C@H](C(N[C@H](CCCN)C(N[C@@]([C@H](O)C)([H])C(N[C@@H](C%12=CC=C(O)C=C%12)C(N[C@H](C%13=CC=C(O)C=C%13)C(NC([C@H](C)O)C(N[C@@H](CC%14=CC=CC=C%14)C(N[C@H](CCCN)C(N[C@@H](C%15=CC=C(O[C@H]%16O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%16O[C@]%17([H])[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O%17)C=C%15)C%18=O)=O)=O)=O)=O)=O)=O)=O)=O)NC([C@@H](NC([C@@H](NC(/C=C\C=C\CC(C)C)=O)CC(N)=O)=O)[C@@H](C(N)=O)OC([C@]([H])(C%19=CC=C(O)C(Cl)=C%19)NC([C@@H](C)NC([C@H](CC(C)C)NC(CNC([C@H](C%20=CC=C(O)C=C%20)NC([C@]([C@H](O)C)([H])N%18)=O)=O)=O)=O)=O)=O)=O.OC(C=C%21)=CC=C%21[C@H](C(N[C@H](CCCN)C(N[C@@]([C@H](O)C)([H])C(N[C@@H](C%22=CC=C(O)C=C%22)C(N[C@H](C%23=CC=C(O)C=C%23)C(NC([C@H](C)O)C(N[C@@H](CC%24=CC=CC=C%24)C(N[C@H](CCCN)C(N[C@@H](C%25=CC=C(O[C@H]%26O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%26O[C@]%27([H])[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O%27)C=C%25)C%28=O)=O)=O)=O)=O)=O)=O)=O)=O)NC([C@@H](NC([C@@H](NC(/C=C\C=C\CCC(C)C)=O)CC(N)=O)=O)[C@@H](C(N)=O)OC([C@]([H])(C%29=CC=C(O)C(Cl)=C%29)NC([C@@H](C)NC([C@H](CC(C)C)NC(CNC([C@H](C%30=CC=C(O)C=C%30)NC([C@]([C@H](O)C)([H])N%28)=O)=O)=O)=O)=O)=O)=O
InChi Code
InChI=1S/C120H156ClN21O40.C119H154ClN21O40.C118H152ClN21O40/c1-55(2)18-12-9-10-15-23-83(154)128-78(51-82(124)153)108(167)142-94-100(102(125)161)181-118(177)93(67-34-45-79(152)73(121)50-67)141-103(162)57(5)127-106(165)76(48-56(3)4)129-84(155)52-126-109(168)88(62-24-35-68(148)36-25-62)137-112(171)87(60(8)147)135-114(173)90(66-32-43-72(44-33-66)178-120-101(98(159)96(157)81(54-144)180-120)182-119-99(160)97(158)95(156)80(53-143)179-119)136-105(164)74(21-16-46-122)130-107(166)77(49-61-19-13-11-14-20-61)132-110(169)85(58(6)145)134-115(174)91(64-28-39-70(150)40-29-64)139-116(175)92(65-30-41-71(151)42-31-65)138-111(170)86(59(7)146)133-104(163)75(22-17-47-123)131-113(172)89(140-117(94)176)63-26-37-69(149)38-27-63;1-54(2)17-11-9-14-22-82(153)127-77(50-81(123)152)107(166)141-93-99(101(124)160)180-117(176)92(66-33-44-78(151)72(120)49-66)140-102(161)56(5)126-105(164)75(47-55(3)4)128-83(154)51-125-108(167)87(61-23-34-67(147)35-24-61)136-111(170)86(59(8)146)134-113(172)89(65-31-42-71(43-32-65)177-119-100(97(158)95(156)80(53-143)179-119)181-118-98(159)96(157)94(155)79(52-142)178-118)135-104(163)73(20-15-45-121)129-106(165)76(48-60-18-12-10-13-19-60)131-109(168)84(57(6)144)133-114(173)90(63-27-38-69(149)39-28-63)138-115(174)91(64-29-40-70(150)41-30-64)137-110(169)85(58(7)145)132-103(162)74(21-16-46-122)130-112(171)88(139-116(93)175)62-25-36-68(148)37-26-62;1-8-9-10-11-15-22-81(152)126-76(50-80(122)151)106(165)140-92-98(100(123)159)179-116(175)91(65-33-44-77(150)71(119)49-65)139-101(160)55(4)125-104(163)74(47-54(2)3)127-82(153)51-124-107(166)86(60-23-34-66(146)35-24-60)135-110(169)85(58(7)145)133-112(171)88(64-31-42-70(43-32-64)176-118-99(96(157)94(155)79(53-142)178-118)180-117-97(158)95(156)93(154)78(52-141)177-117)134-103(162)72(20-16-45-120)128-105(164)75(48-59-18-13-12-14-19-59)130-108(167)83(56(5)143)132-113(172)89(62-27-38-68(148)39-28-62)137-114(173)90(63-29-40-69(149)41-30-63)136-109(168)84(57(6)144)131-102(161)73(21-17-46-121)129-111(170)87(138-115(92)174)61-25-36-67(147)37-2
InChi Key
QQYIBSSNSBPSCP-SBEAELFISA-N
Origin
Bacterium/Actinoplanes sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ramoplanin complex is a mixture of ramoplanin A1, -A2, and -A3 originally isolated from Actinoplanes that has antibacterial activity.1,2,3 Ramoplanin complex is active against clinical isolates of the Gram-positive bacteria S. aureus, S. pyogenes, S. pneumoniae, and S. faecalis (MICs = 0.016-2 µg/ml) but not Gram-negative bacteria or C. albicans (MICs = ≥128 µg/ml).2 It inhibits cell wall synthesis in B. subtilis when used at a concentration of 0.5 µg/ml.1 Ramoplanin complex is effective against systemic S. pyogenes, S. pneumoniae, and S. aureus infections in mice with ED50 values of 0.081, 0.14, and approximately 25 mg/kg per day, respectively.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cavalleri, B., Pagani, H., Volpe, G., et al. A-16686, a new antibiotic from actinoplanes. I. Fermentation, isolation and preliminary physico-chemical characteristics. J. Antibiot. (Tokyo) 37(4), 309-317 (1984).

    2. Pallanza, R., Berti, M., Scotti, R., et al. A-16686, a new antibiotic from actinoplanes. II. Biological properties. J. Antibiot. (Tokyo) 37(4), 318-324 (1984).

    3. Shin, D., Rew, Y., and Boger, D.L. Total synthesis and structure of the ramoplanin A1 and A3 aglycons: Two minor components of the ramoplanin complex. Proc. Natl. Acad. Sci. USA 101(33), 11977-11979 (2004).