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CRAMP-18 (mouse)

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CRAMP-18 (mouse) corresponds to the functional region of the antimicrobial peptide CRAMP and has strong antibacterial activity against a variety of bacteria, with no hemolytic activity (MIC = 12.5-50 μM).

Category

Functional Peptides

Catalog number

BAT-015369

CAS number

256639-17-5

Molecular Formula

C101H171N27O24

Molecular Weight

2147.64

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S)-6-amino-2-[[(2S)-5-amino-2-[[2-[[(2S,3S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-4-carboxybutanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]hexanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]-5-oxopentanoyl]amino]hexanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-5-oxopentanoyl]amino]hexanoyl]amino]-4-methylpentanoic acid

Synonyms

H-Gly-Glu-Lys-Leu-Lys-Lys-Ile-Gly-Gln-Lys-Ile-Lys-Asn-Phe-Phe-Gln-Lys-Leu-OH; glycyl-L-alpha-glutamyl-L-lysyl-L-leucyl-L-lysyl-L-lysyl-L-isoleucyl-glycyl-L-glutaminyl-L-lysyl-L-isoleucyl-L-lysyl-L-asparagyl-L-phenylalanyl-L-phenylalanyl-L-glutaminyl-L-lysyl-L-leucine

Appearance

White or Off-white Lyophilized Powder

Purity

95%

Sequence

GEKLKKIGQKIKNFFQKL

Storage

Store at -20°C

Solubility

Soluble in DMSO

InChI

InChI=1S/C101H171N27O24/c1-9-60(7)84(127-93(143)68(37-21-27-49-106)117-86(136)64(33-17-23-45-102)119-95(145)73(51-58(3)4)122-87(137)65(34-18-24-46-103)115-91(141)71(41-44-83(134)135)113-81(132)56-108)99(149)112-57-82(133)114-70(39-42-78(109)129)90(140)118-69(38-22-28-50-107)94(144)128-85(61(8)10-2)100(150)121-67(36-20-26-48-105)88(138)125-76(55-80(111)131)98(148)124-75(54-63-31-15-12-16-32-63)97(147)123-74(53-62-29-13-11-14-30-62)96(146)120-72(40-43-79(110)130)92(142)116-66(35-19-25-47-104)89(139)126-77(101(151)152)52-59(5)6/h11-16,29-32,58-61,64-77,84-85H,9-10,17-28,33-57,102-108H2,1-8H3,(H2,109,129)(H2,110,130)(H2,111,131)(H,112,149)(H,113,132)(H,114,133)(H,115,141)(H,116,142)(H,117,136)(H,118,140)(H,119,145)(H,120,146)(H,121,150)(H,122,137)(H,123,147)(H,124,148)(H,125,138)(H,126,139)(H,127,143)(H,128,144)(H,134,135)(H,151,152)/t60-,61-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,84-,85-/m0/s1

InChI Key

OZVCRGKXXWONLP-YTSNNXBCSA-N

Canonical SMILES

CCC(C)C(C(=O)NCC(=O)NC(CCC(=O)N)C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(CCC(=O)N)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)O)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)CN

1. CRAMP analog having potent antibiotic activity without hemolytic activity

Jae Il Kim, Kyung-Soo Hahm, Dong Gun Lee, Yangmee Kim, Song Yub Shin, Shin-Won Kang, Sung-Tae Yang Protein Pept Lett . 2002 Aug;9(4):275-82. doi: 10.2174/0929866023408643.

CRAMP-18 is an 18-residue functional region, corresponding to residues 16-33 of a mouse-derived antibiotic peptide CRAMP. To develop novel antibiotic peptides possessing strong antibiotic activity against bacterial, fungal and tumor cells without hemolytic activity, three analogs of CRAMP-18 were synthesized containing either Leu- or Lys-substitution. Leu-substitution ([L(1, 8)]-CRAMP-18) in the hydrophobic helix face of CRAMP-18 induced a dramatic increase in antibiotic activity without a significant increase in hemolytic activity. Lys-substitution ([K(2, 13)]-CRAMP-18 or [K(9, 16)]-CRAMP-18) in the hydrophilic helix face produced a smaller response. Therefore, [L(1, 8)]-CRAMP-18 may be an attractive candidate for developing novel peptide antibiotics.