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Rhodopeptin C1

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Category Bioactive by-products
Catalog number BBF-02192
CAS
Molecular Weight 481.67
Molecular Formula C25H47N5O4

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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

Rhodopeptin C1 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-(7-methylnonyl)-1,4,7,10-tetrazacyclotridecane-2,5,8,11-tetrone
IUPAC Name (3S,6S)-6-(3-aminopropyl)-13-(7-methylnonyl)-3-propan-2-yl-1,4,7,10-tetrazacyclotridecane-2,5,8,11-tetrone
Canonical SMILES CCC(C)CCCCCCC1CC(=O)NCC(=O)NC(C(=O)NC(C(=O)N1)C(C)C)CCCN
InChI InChI=1S/C25H47N5O4/c1-5-18(4)11-8-6-7-9-12-19-15-21(31)27-16-22(32)29-20(13-10-14-26)24(33)30-23(17(2)3)25(34)28-19/h17-20,23H,5-16,26H2,1-4H3,(H,27,31)(H,28,34)(H,29,32)(H,30,33)/t18?,19?,20-,23-/m0/s1
InChI Key BCORRXOGBNOQQU-NWEKGRFWSA-N
Appearance White Powder
Antibiotic Activity Spectrum fungi
Boiling Point 791.3±60.0°C at 760 mmHg
Melting Point >240°C
Density 1.0±0.1 g/cm3
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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