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Arborcandin A

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Category Enzyme inhibitors
Catalog number BBF-00072
CAS
Molecular Weight 1256.48
Molecular Formula C57H101N13O18

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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

Arborcandins are 1,3-β-glucan synthase inhibitors produced by the filamentous fungus SANK 17397.

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Synonyms 21,24-Bis(carbamoylmethyl)-15-(2-carbamoyl-2-hydroxyethyl)-9,12-bis(1-hydroxyethyl)-6-(3-hydroxydodecyl)-27-(8-hydroxydodecyl)-18-methyl-1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontane-2,5,8,11,14,17,20,23,26,29-decone
IUPAC Name 3-[5,8-bis(2-amino-2-oxoethyl)-23-(3-hydroxydodecyl)-2-(8-hydroxydodecyl)-17,20-bis(1-hydroxyethyl)-11-methyl-3,6,9,12,15,18,21,24,27,31-decaoxo-1,4,7,10,13,16,19,22,25,28-decazacyclohentriacont-14-yl]-2-hydroxypropanamide
Canonical SMILES CCCCCCCCCC(CCC1C(=O)NCC(=O)NCCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C(C)O)C(C)O)CC(C(=O)N)O)C)CC(=O)N)CC(=O)N)CCCCCCCC(CCCC)O)O
InChI InChI=1S/C57H101N13O18/c1-6-8-10-11-12-14-18-22-36(74)24-25-38-51(82)62-31-46(79)61-27-26-45(78)64-37(23-19-16-13-15-17-21-35(73)20-9-7-2)52(83)67-41(30-44(59)77)54(85)68-40(29-43(58)76)53(84)63-32(3)50(81)66-39(28-42(75)49(60)80)55(86)69-48(34(5)72)57(88)70-47(33(4)71)56(87)65-38/h32-42,47-48,71-75H,6-31H2,1-5H3,(H2,58,76)(H2,59,77)(H2,60,80)(H,61,79)(H,62,82)(H,63,84)(H,64,78)(H,65,87)(H,66,81)(H,67,83)(H,68,85)(H,69,86)(H,70,88)
InChI Key YALGAPDBNREBKQ-UHFFFAOYSA-N
Appearance Colorless Powder
1. Arborcandins A, B, C, D, E and F, novel 1,3-beta-glucan synthase inhibitors: production and biological activity
T Ohyama, Y Kurihara, Y Ono, T Ishikawa, S Miyakoshi, K Hamano, M Arai, T Suzuki, H Igari, Y Suzuki, M Inukai J Antibiot (Tokyo). 2000 Oct;53(10):1108-16. doi: 10.7164/antibiotics.53.1108.
Arborcandins A, B, C, D, E and F, which possess potent 1,3-beta-glucan synthase inhibitory activity, were isolated from the culture broth of a filamentous fungus, strain SANK 17397. Arborcandins are novel cyclic peptides, that are structurally different from known glucan synthase inhibitors such as echinocandins. The 1,3-beta-glucan synthases of Candida albicans and Aspergillus fumigatus were inhibited by arborcandins with IC50 ranging from 0.012 to 3 microg/ml. The apparent Ki value of arborcandin C for C. albicans and A. fumigatus were 0.12 microM and 0.016 microM, respectively. The inhibition against these two 1,3-beta-glucan synthases by arborcandin C was noncompetitive. These compounds exhibited potent fungicidal activity against Candida spp. with MIC ranging from 0.25 to 8 microg/ml. The growth of A. fumigatus was suppressed by arborcandins with concentrations ranging from 0.063 to 4 microg/ml.
2. FKS1 mutations responsible for selective resistance of Saccharomyces cerevisiae to the novel 1,3-beta-glucan synthase inhibitor arborcandin C
Takao Ohyama, Shunichi Miyakoshi, Fujio Isono Antimicrob Agents Chemother. 2004 Jan;48(1):319-22. doi: 10.1128/AAC.48.1.319-322.2004.
Arborcandin C is a novel antibiotic with potent antifungal activity that inhibits 1,3-beta-glucan synthase in fungi. We examined spontaneous Saccharomyces cerevisiae mutants which are selectively resistant to arborcandin C and revealed that a single amino acid replacement in Fks1p of Asn(470) with Lys or of Leu(642) with Ser confers selective resistance on Fks1p mutants.
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