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Chrysospermin A

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Category Antibiotics
Catalog number BBF-00330
CAS 160824-57-7
Molecular Weight 1898.20
Molecular Formula C90H140N22O23

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

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

It is produced by the strain of Apiocrea chrysosperma Ap101. Chrysospermin A has antibacterial activities against individual gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis), Klebsiella pneumoniae and individual yeasts (Ocher echinoderma, saccharomyces cerevisiae).

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IUPAC Name (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-1,3-dihydroxy-2-[[1-hydroxy-2-[[(2S)-1-hydroxy-2-(1-hydroxyethylideneamino)-3-phenylpropylidene]amino]-2-methylpropylidene]amino]propylidene]amino]-1-hydroxy-2-methylpropylidene]amino]-1-hydroxy-2-methylpropylidene]amino]-1-hydroxy-4-methylpentylidene]amino]-N-[2-[1-[1-[(2S)-1-[(2S)-1-[1-[(2S)-2-[N-[1-[1-[1-[(2S)-1,5-dihydroxy-1-[(2S)-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]imino-5-iminopentan-2-yl]imino-1-hydroxy-2-methylpropan-2-yl]imino-1-hydroxy-2-methylpropan-2-yl]imino-1-hydroxy-2-methylpropan-2-yl]-C-hydroxycarbonimidoyl]pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl]imino-1-hydroxypropan-2-yl]imino-1-hydroxypropan-2-yl]imino-1-hydroxy-2-methylpropan-2-yl]imino-1-hydroxy-2-methylpropan-2-yl]imino-2-hydroxyethyl]pentanediimidic acid
Canonical SMILES CC(C)CC(C(=NC(CCC(=N)O)C(=NCC(=NC(C)(C)C(=NC(C)(C)C(=NC(C)C(=NC(C)C(=NC(C)(C)C(=O)N1CCCC1C(=NC(C)(C)C(=NC(C)(C)C(=NC(C)(C)C(=NC(CCC(=N)O)C(=NC(CC2=CNC3=CC=CC=C32)CO)O)O)O)O)O)O)O)O)O)O)O)O)N=C(C(C)(C)N=C(C(C)(C)N=C(C(CO)N=C(C(C)(C)N=C(C(CC4=CC=CC=C4)N=C(C)O)O)O)O)O)O
InChI InChI=1S/C90H140N22O23/c1-47(2)40-58(101-76(130)85(12,13)109-78(132)87(16,17)106-71(125)60(46-114)102-74(128)82(6,7)105-70(124)59(97-50(5)115)41-51-30-25-24-26-31-51)69(123)99-56(35-37-62(91)116)67(121)94-44-64(118)103-86(14,15)77(131)108-83(8,9)73(127)96-48(3)65(119)95-49(4)66(120)104-90(22,23)81(135)112-39-29-34-61(112)72(126)107-88(18,19)79(133)111-89(20,21)80(134)110-84(10,11)75(129)100-57(36-38-63(92)117)68(122)98-53(45-113)42-52-43-93-55-33-28-27-32-54(52)55/h24-28,30-33,43,47-49,53,56-61,93,113-114H,29,34-42,44-46H2,1-23H3,(H2,91,116)(H2,92,117)(H,94,121)(H,95,119)(H,96,127)(H,97,115)(H,98,122)(H,99,123)(H,100,129)(H,101,130)(H,102,128)(H,103,118)(H,104,120)(H,105,124)(H,106,125)(H,107,126)(H,108,131)(H,109,132)(H,110,134)(H,111,133)/t48-,49-,53-,56-,57-,58-,59-,60-,61-/m0/s1
InChI Key GIZISGRBTRFGIJ-WNMUOJPCSA-N
Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria; yeast
Melting Point 250 °C
1. Chrysospermins, new peptaibol antibiotics from Apiocrea chrysosperma Ap101
K Dornberger, W Ihn, M Ritzau, U Gräfe, B Schlegel, W F Fleck, J W Metzger J Antibiot (Tokyo). 1995 Sep;48(9):977-89. doi: 10.7164/antibiotics.48.977.
Four new members of peptaibol antibiotics, designated as chrysospermins A, B, C, and D, were isolated from the mycelium of Apiocrea chrysosperma Ap101 by solvent extraction, silica gel chromatography and preparative recycling HPLC. Their structures as new nonadecapeptides were settled by detailed spectroscopic analysis and chemical degradation experiments. The chrysospermins display antibacterial and antifungal activity, and induce pigment formation by the fungus Phoma destructiva.
2. Effective diameters of ion channels formed by homologs of the antibiotic chrysospermin
V I Ternovsky, P A Grigoriev, G N Berestovsky, R Schlegel, K Dornberger, U Gräfe Membr Cell Biol. 1997;11(4):497-505.
Radii of ion channels formed in the lipid bilayer by 4 homologs of the alamethicin-like antibiotic, chrysospermin, were determined using hydrophilic nonelectrolytes. It is shown that the replacement of isovaline amino acid at position 15 of the polypeptide chain by alpha-aminoisobutyric acid results in the decrease in the channel effective radius from 1.2 +/- 0.15 to 0.94 +/- 0.1 nm and a respective 2.5-fold decrease in channel conductance.

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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