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Kassinatuerin-2

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Kassinatuerin-2 is an antibacterial peptide isolated from Kassina senegalensis (Senegal running frog). It has activity against gram-positive bacteria, gram-negative bacteria and fungi.

Category

Functional Peptides

Catalog number

BAT-012535

Molecular Formula

C108H173N25O25

Molecular Weight

2221.72

Specification
Reference Reading

IUPAC Name

(3S)-3-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S,3S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-methylpentanoyl]amino]-5-oxopentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-4-[[(2S)-1-[[(2S,3S)-1-amino-3-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-oxobutanoic acid

Synonyms

H-Phe-Ile-Gln-Tyr-Leu-Ala-Pro-Leu-Ile-Pro-His-Ala-Val-Lys-Ala-Ile-Ser-Asp-Leu-Ile-NH2

Purity

95.8%

Sequence

FIQYLAPLIPHAVKAISDLI-NH2

Storage

Store at -20°C

InChI

InChI=1S/C108H173N25O25/c1-20-59(13)85(89(112)139)128-99(149)74(46-56(7)8)121-98(148)78(51-83(137)138)123-101(151)79(53-134)126-106(156)86(60(14)21-2)129-91(141)64(18)115-93(143)71(33-27-28-42-109)118-104(154)84(58(11)12)127-90(140)63(17)116-96(146)77(50-68-52-113-54-114-68)125-103(153)81-35-30-44-133(81)108(158)88(62(16)23-4)131-100(150)75(47-57(9)10)124-102(152)80-34-29-43-132(80)107(157)65(19)117-95(145)73(45-55(5)6)120-97(147)76(49-67-36-38-69(135)39-37-67)122-94(144)72(40-41-82(111)136)119-105(155)87(61(15)22-3)130-92(142)70(110)48-66-31-25-24-26-32-66/h24-26,31-32,36-39,52,54-65,70-81,84-88,134-135H,20-23,27-30,33-35,40-51,53,109-110H2,1-19H3,(H2,111,136)(H2,112,139)(H,113,114)(H,115,143)(H,116,146)(H,117,145)(H,118,154)(H,119,155)(H,120,147)(H,121,148)(H,122,144)(H,123,151)(H,124,152)(H,125,153)(H,126,156)(H,127,140)(H,128,149)(H,129,141)(H,130,142)(H,131,150)(H,137,138)/t59-,60-,61-,62-,63-,64-,65-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,84-,85-,86-,87-,88-/m0/s1

InChI Key

MQRMIDJSNPMZQS-YNYUXEIOSA-N

Canonical SMILES

CCC(C)C(C(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)CC)NC(=O)C(C)NC(=O)C(CCCCN)NC(=O)C(C(C)C)NC(=O)C(C)NC(=O)C(CC1=CN=CN1)NC(=O)C2CCCN2C(=O)C(C(C)CC)NC(=O)C(CC(C)C)NC(=O)C3CCCN3C(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)CC)NC(=O)C(CC5=CC=CC=C5)N

1. Kassinatuerin-1: a peptide with broad-spectrum antimicrobial activity isolated from the skin of the hyperoliid frog, Kassina senegalensis

B Mattute, F C Knoop, J M Conlon Biochem Biophys Res Commun. 2000 Feb 16;268(2):433-6. doi: 10.1006/bbrc.2000.2136.

Kassinatuerin-1 (GFMKYIGPLI(10)PHAVKAISDL(20)I.NH(2)) was isolated in high yield (75 nmol/g) from an extract of the skin of a Hyperoliid frog, the African running frog Kassina senegalensis and its sequence was confirmed by total synthesis. The peptide inhibited growth of the gram-negative bacterium Escherichia coli (minimum inhibitory concentration, MIC = 4 microM), the gram-positive bacterium Staphylococcus aureus (MIC = 8 microM), and the yeast Candida albicans (MIC = 70 microM). A structurally related peptide, kassinatuerin-2 (FIQYLAPLI(10)PHAVKAISDL(20)I.NH(2)) was also isolated in high yield (96 nmol/g) from the extract but was devoid of antimicrobial activity against these microrganisms. Kassinatuerin-1 may be classified with other linear, cationic antimicrobial peptides that can potentially adopt an amphipathic alpha-helical conformation but it contains almost no amino acid sequence identity with previously characterized bioactive peptides from frog skin.

2. A family of kassinatuerin-2 related peptides from the skin secretion of the African hyperoliid frog, Kassina maculata

Lei Wang, Mei Zhou, Stephanie McGrath, Tianbao Chen, Sean P Gorman, Brian Walker, Chris Shaw Peptides. 2009 Aug;30(8):1428-33. doi: 10.1016/j.peptides.2009.04.021. Epub 2009 May 7.

We describe the isolation and structural characterization of a family of antimicrobial peptides related to kassinatuerin-2, from the skin secretion of the African hyperoliid frog, Kassina maculata. All four peptides, designated kassinatuerin-2Ma through Md, are C-terminally-amidated 20-mers with the consensus sequence - FX(1)GAIAAALPHVIX(2)AIKNAL - where X(1)=L/F/V/I and X2=S/N. All four peptides are encoded by precursors of 69 amino acids. Synthetic replicates of all kassinatuerin-2 related peptides displayed a potent inhibitory activity against Staphylococcus aureus with a minimal inhibitory concentration of 16microM, at which concentration, however, they effected 18% haemolysis of horse erythrocytes after 2h. Despite obvious membranolytic properties, all peptides were ineffective at inhibiting the growth of Escherichia coli at concentrations up to 200microM and were relatively ineffective against Candida albicans (MIC 120microM). The kassinatuerin-2 related peptides of K. maculata skin secretion thus possess a discrete antimicrobial and weak haemolytic activity in contrast to the prototype kassinatuerin-2 from the skin secretion of Kassina senegalensis.