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Rhodopeptin C2

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Rhodopeptin C2
Category Bioactive by-products
Catalog number BBF-02193
CAS
Molecular Weight 495.70
Molecular Formula C26H49N5O4

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4 R&D and scale-up labs

2 Preparative purification labs

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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 C2 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)-13-(7-methylnonyl)-3-sec-butyl-1,4,7,10-tetrazacyclotridecane-2,5,8,11-tetrone
IUPAC Name (3S,6S)-6-(3-aminopropyl)-3-butan-2-yl-13-(7-methylnonyl)-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)CC)CCCN
InChI InChI=1S/C26H49N5O4/c1-5-18(3)12-9-7-8-10-13-20-16-22(32)28-17-23(33)30-21(14-11-15-27)25(34)31-24(19(4)6-2)26(35)29-20/h18-21,24H,5-17,27H2,1-4H3,(H,28,32)(H,29,35)(H,30,33)(H,31,34)/t18?,19?,20?,21-,24-/m0/s1
InChI Key ITBKUPNSNYDPST-YEUCXLETSA-N
Appearance Colorless Solid
Antibiotic Activity Spectrum fungi
1. 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.
2. 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.

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