Actagardin
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| Category | Antibiotics |
| Catalog number | BBF-04201 |
| CAS | 59165-34-3 |
| Molecular Weight | 1754.03 |
| Molecular Formula | C81H132N20O23 |
| Purity | >98% by HPLC |
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Description
It is a peptide antibiotic produced by several species of actinoplanes. It has the activity against Gram-positive and Gram-negative bacteria. It inhibits the biosynthesis of peptidoglycan.
Specification
| Synonyms | Actagardine; Antibiotic A 3802-IV-3; Gardimycin; D-Cysteinyl-L-serylglycyl-L-tryptophyl-L-valyl-L-cysteinyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-leucyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-isoleucyl-L-α-glutamyl-L-cysteinylglycyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-valyl-L-isoleucyl-L-cysteinyl-L-alanyl-L-cysteine S14-Oxide; H-D-Ala-Leu-D-Abu-Ile-D-Glu-D-Abu-D-Ala-Val-D-Trp-Gly-D-Ser-D-Ala-Gly-D-Abu-Val-Ile-D-Ala-Ala-D-Ala-OH |
| Sequence | ALXIEXAVWGSAGXVIAAA |
| Storage | Store at -20°C |
| IUPAC Name | (4R)-4-[[(2S,3S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-aminopropanoyl]amino]-4-methylpentanoyl]amino]butanoyl]amino]-3-methylpentanoyl]amino]-5-[[(2R)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[2-[[(2R)-1-[[(2R)-1-[[2-[[(2R)-1-[[(2S)-1-[[(2S,3S)-1-[[(2R)-1-[[(2S)-1-[[(1R)-1-carboxyethyl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxobutan-2-yl]amino]-5-oxopentanoic acid |
| Canonical SMILES | CCC(C)C(C(=O)NC(CCC(=O)O)C(=O)NC(CC)C(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NCC(=O)NC(CO)C(=O)NC(C)C(=O)NCC(=O)NC(CC)C(=O)NC(C(C)C)C(=O)NC(C(C)CC)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C)C(=O)O)NC(=O)C(CC)NC(=O)C(CC(C)C)NC(=O)C(C)N |
| InChI | InChI=1S/C81H132N20O23/c1-20-40(12)63(79(121)89-45(17)67(109)86-44(16)68(110)90-47(19)81(123)124)101-78(120)62(39(10)11)99-72(114)50(22-3)91-58(103)34-84-66(108)43(15)87-76(118)57(36-102)92-59(104)35-85-70(112)56(32-48-33-83-53-28-26-25-27-49(48)53)97-77(119)61(38(8)9)98-69(111)46(18)88-71(113)51(23-4)93-74(116)54(29-30-60(105)106)95-80(122)64(41(13)21-2)100-73(115)52(24-5)94-75(117)55(31-37(6)7)96-65(107)42(14)82/h25-28,33,37-47,50-52,54-57,61-64,83,102H,20-24,29-32,34-36,82H2,1-19H3,(H,84,108)(H,85,112)(H,86,109)(H,87,118)(H,88,113)(H,89,121)(H,90,110)(H,91,103)(H,92,104)(H,93,116)(H,94,117)(H,95,122)(H,96,107)(H,97,119)(H,98,111)(H,99,114)(H,100,115)(H,101,120)(H,105,106)(H,123,124)/t40-,41-,42+,43+,44-,45+,46+,47+,50+,51+,52+,54+,55-,56+,57+,61-,62-,63-,64-/m0/s1 |
| InChI Key | LAWKVNVCUPIOMG-HWWYPGLISA-N |
| Source | Actinoplanes sp. |
Properties
| Appearance | White to Off-white Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 2194.7±65.0°C (Predicted) |
| Density | 1.42±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. [Isolation and identification of antibiotics produced by Actinoplanes brasiliensis INA 3802]
N M Arkhangel'skaia, G B Fedorova, G S Katrukha, A V Laĭko, M Iassein, Zh P Trifonova Antibiot Khimioter . 1999;44(5):6-11.
In the screening programme for new antibiotics produced by Actinoplanes brasiliensis an antibiotic complex A-3802 was isolated and studied in detail. It had a marked therapeutic effect in the treatment of staphylococcal sepsis in albino mice and was low toxic. Two components of the complex i.e. A-3802-IV-3 and A-3802-IV-4 were identified with the lantibiotics actagardin and its diamide disulfoxide. Antibiotics A-3802-V-4 and A-3802-VI-7 were shown to be new antibiotics of the same group.
2. [Actinoplanes brasiliensis INA 3802--a producer of peptide antibiotics]
Iu I Kozlova, I V Tolstykh, O A Galatenko, L P Terekhova, I G Sumarukova, T P Golova, A V Laĭko Antibiot Khimioter . 1999;44(4):5-8.
In the screening programme for new antibiotics an actinomycete culture designated as 3802 was isolated from a soil sample. The culture produced a complex of peptide antibiotics belonging to the group of lantibiotics. The antibiotic complex included gardimycin (actagardin) and new antibiotics of the same group. By the taxonomic properties strain 3802 was classified as Actinoplanes brasiliensis not previously known to produce gardimycin. Conditions of the antibiotic complex biosynthesis by strain 3802, the isolation methods and biological properties were studied.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
