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Rhodopeptin C3

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Category Bioactive by-products
Catalog number BBF-02194
CAS
Molecular Weight 495.70
Molecular Formula C26H49N5O4

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Product Description

Rhodopeptin C3 is a cyclic tetrapeptide originally isolated from Rhodococcus sp. Mer-N1033. It has anti-candida and cryptococcus neoformant activities, and the MIC (μg/mL) was 1.25~2.5 and 0.63~1.25, respectively.

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Synonyms (3S,6S)-6-(3-aminopropyl)-3-isopropyl-13-(9-methyldecyl)-1,4,7,10-tetrazacyclotridecane-2,5,8,11-tetrone
IUPAC Name (3S,6S)-6-(3-aminopropyl)-13-(9-methyldecyl)-3-propan-2-yl-1,4,7,10-tetrazacyclotridecane-2,5,8,11-tetrone
Canonical SMILES CC(C)CCCCCCCCC1CC(=O)NCC(=O)NC(C(=O)NC(C(=O)N1)C(C)C)CCCN
InChI InChI=1S/C26H49N5O4/c1-18(2)12-9-7-5-6-8-10-13-20-16-22(32)28-17-23(33)30-21(14-11-15-27)25(34)31-24(19(3)4)26(35)29-20/h18-21,24H,5-17,27H2,1-4H3,(H,28,32)(H,29,35)(H,30,33)(H,31,34)/t20?,21-,24-/m0/s1
InChI Key SCHMCJIVWBGMAV-AVJWOPLCSA-N
Appearance Colorless Solid
Antibiotic Activity Spectrum fungi
1. Rhodopeptins, novel cyclic tetrapeptides with antifungal activities from Rhodococcus sp. II. Structure elucidation
H Chiba, H Agematu, K Dobashi, T Yoshioka J Antibiot (Tokyo). 1999 Aug;52(8):700-9. doi: 10.7164/antibiotics.52.700.
The structures of rhodopeptins, novel antifungal peptides, were determined on the basis of physico-chemical analyses of the intact molecules and their acid hydrolysates. The structures of rhodopeptins C1, C2, C3, C4 and B5 were determined to be cyclo (-Gly-L-Orn-L-Val-3-amino-10-methyldodecanoyl-), cyclo (-Gly-L-Orn-L-Ile-3-amino-10-methyldodecanoyl-), cyclo (-Gly-L-Orn-L-Val-3-amino-12-methyltridecanoyl-), cyclo (-Gly-L-Orn-L-Val-3-amino- 12-methyltetradecanoyl-) and cyclo (-Gly-L-Lys-L-Val-3-amino-13-methyltetradecanoyl-), respectively. They are novel cyclic tetrapeptides containing a lipophilic beta-amino acid.
2. Rhodopeptins (Mer-N1033), novel cyclic tetrapeptides with antifungal activity from Rhodococcus sp. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
H Chiba, H Agematu, R Kaneto, T Terasawa, K Sakai, K Dobashi, T Yoshioka J Antibiot (Tokyo). 1999 Aug;52(8):695-9. doi: 10.7164/antibiotics.52.695.
Five novel cyclic tetrapeptides, named rhodopeptin C1, C2, C3, C4 and B5, were isolated from a strain named Rhodococcus sp. Mer-N1033. They are a novel type of cyclic tetrapeptide composed of a beta-amino acid and three usual alpha-amino acids. Rhodopeptins show high in vitro antifungal activity against Candida albicans and Cryptococcus neoformans, whereas they show no activity against bacteria.

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