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Ranatuerin-2CSa

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Ranatuerin-2CSa is an antimicrobial peptide first isolated from skin secretions of the Cascades frog, Rana cascadae. It shows potent growth inhibitory activity against Escherichia coli (MIC=5 microM) and Staphylococcus aureus (MIC=10 microM), and has haemolytic activity against human erythrocytes (LC50=160 microM).

Category

Functional Peptides

Catalog number

BAT-011408

Molecular Formula

C145H252N38O41S2

Molecular Weight

3247.96

Specification
Reference Reading

IUPAC Name

(3S,6S,9S,15S,18S,21S,24S)-24-(((2S,3R)-1-(((S)-1-(((S)-6-amino-1-(((4R,10S,13S,16S,19R)-16-(4-aminobutyl)-13-((S)-sec-butyl)-4-carboxy-10-((R)-1-hydroxyethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl)amino)-1-oxohexan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-3-hydroxy-1-oxobutan-2-yl)carbamoyl)-3-((2S,5S,8S,14S,17S,20S,26S,29S,32S,35S,38S,41S)-44-amino-2,14,26-tris(4-aminobutyl)-29-benzyl-41-((S)-sec-butyl)-32,35-bis(hydroxymethyl)-38-isobutyl-8,20-diisopropyl-5,17-dimethyl-4,7,10,13,16,19,22,25,28,31,34,37,40,43-tetradecaoxo-3,6,9,12,15,18,21,24,27,30,33,36,39,42-tetradecaazatetratetracontanamido)-15-(4-aminobutyl)-6,18,21-triisobutyl-9-methyl-4,7,10,13,16,19,22-heptaoxo-5,8,11,14,17,20,23-heptaazaheptacosanedioic acid

Synonyms

Gly-Ile-Leu-Ser-Ser-Phe-Lys-Gly-Val-Ala-Lys-Gly-Val-Ala-Lys-Asp-Leu-Ala-Gly-Lys-Leu-Leu-Glu-Thr-Leu-Lys-Cys-Lys-Ile-Thr-Gly-Cys (Disulfide bridge: Cys27-Cys32)

Appearance

Powder

Purity

≥96%

Sequence

GILSSFKGVAKGVAKDLAGKLLETLKCKITGC (Disulfide bridge: Cys27-Cys32)

Storage

Store at -20°C

1. Peptide defenses of the Cascades frog Rana cascadae: implications for the evolutionary history of frogs of the Amerana species group

J Michael Conlon, et al. Peptides. 2007 Jun;28(6):1268-74. doi: 10.1016/j.peptides.2007.03.010. Epub 2007 Mar 27.

The Cascades frog Rana cascadae belongs to the Amerana (or Rana boylii) group that includes six additional species from western North America (R. aurora, R. boylii, R. draytonii, R. luteiventris, R. muscosa, and R. pretiosa). R. cascadae is particularly susceptible to pathogenic microorganisms in the environment and populations have declined precipitously in parts of its range so that the protection afforded by dermal antimicrobial peptides may be crucial to survival of the species. Peptidomic analysis of norepinephrine-stimulated skin secretions led to the identification of six peptides with differential cytolytic activities that were present in high abundance. Structural characterization showed that they belonged to the ranatuerin-2 (one peptide), brevinin-1 (one peptide), and temporin (four peptides) families. Ranatuerin-2CSa (GILSSFKGVAKGVAKDLAGKLLETLKCKITGC) and brevinin-1CSa (FLPILAGLAAKIVPKLFCLATKKC) showed broad spectrum antibacterial activity (MIC

2. Conformational analysis of the broad-spectrum antibacterial peptide, ranatuerin-2CSa: identification of a full length helix-turn-helix motif

Anusha P Subasinghage, J Michael Conlon, Chandralal M Hewage Biochim Biophys Acta. 2008 Jun;1784(6):924-9. doi: 10.1016/j.bbapap.2008.02.019. Epub 2008 Mar 14.

Design of clinically valuable antibacterial agents based upon naturally occurring peptides requires the use of spectroscopic methods, particularly NMR, to determine the three-dimensional structure of the native peptide so that analogues with improved therapeutic properties can be made. Ranatuerin-2CSa (GILSSFKGVAKGVAKDLAG KLLETLKCKITGC), first isolated from skin secretions of the Cascades frog, Rana cascadae, represents a promising candidate for drug development. The peptide shows potent growth inhibitory activity against Escherichia coli (MIC=5 microM) and Staphylococcus aureus (MIC=10 microM) but displays haemolytic activity against human erythrocytes (LC(50)=160 microM). The solution structure of ranatuerin-2CSa was investigated by proton NMR spectroscopy and molecular modelling. In aqueous solution, the peptide lacks secondary structure but, in a 2,2,2-trifluoroethanol (TFE-d(3))-H(2)O solvent mixture, the structure is characterised by a full length helix-turn-helix conformation between residues I(2)-L(21), L(22)-L(25) and K(26)-T(30) respectively. This structural information will facilitate the design of novel therapeutic agents based upon the ranatuerin-2CSa structure with improved antimicrobial potencies but decreased cytolytic activities against mammalian cells.