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Penetratin-Arg

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Penetratin-Arg, a cell-penetrating peptide (CPP) derived from the 3rd helix of Drosophila Antennapedia homeodomain protein, can permeate cell membrane at low micromolar concentration without significantly affecting membrane. It contains a nuclear localization sequence that facilitates internalization of cargo into living cells.

Category
Functional Peptides
Catalog number
BAT-013269
Molecular Formula
C104H169N43O19S
Molecular Weight
2357.80
IUPAC Name
(2S)-N-[(2S,3S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]pentanediamide
Synonyms
PenArg; H-Arg-Gln-Ile-Arg-Ile-Trp-Phe-Gln-Asn-Arg-Arg-Met-Arg-Trp-Arg-Arg-NH2; L-arginyl-L-glutaminyl-L-isoleucyl-L-arginyl-L-isoleucyl-L-tryptophyl-L-phenylalanyl-L-glutaminyl-L-asparagyl-L-arginyl-L-arginyl-L-methionyl-L-arginyl-L-tryptophyl-L-arginyl-L-argininamide
Appearance
Lyophilized Solid
Purity
>98%
Density
1.5±0.1 g/cm3
Sequence
RQIRIWFQNRRMRWRR-NH2
Storage
Store at -20°C
Solubility
Soluble in water. Avoid repeated freezing and thawing.
InChI
InChI=1S/C104H169N43O19S/c1-6-54(3)80(147-91(160)71(36-38-78(107)149)134-83(152)61(105)26-15-40-124-98(110)111)96(165)141-69(34-21-46-130-104(122)123)90(159)146-81(55(4)7-2)97(166)145-75(50-58-53-132-63-28-14-12-25-60(58)63)94(163)142-73(48-56-22-9-8-10-23-56)92(161)139-70(35-37-77(106)148)88(157)144-76(51-79(108)150)95(164)138-67(32-19-44-128-102(118)119)85(154)135-66(31-18-43-127-101(116)117)86(155)140-72(39-47-167-5)89(158)136-68(33-20-45-129-103(120)121)87(156)143-74(49-57-52-131-62-27-13-11-24-59(57)62)93(162)137-65(30-17-42-126-100(114)115)84(153)133-64(82(109)151)29-16-41-125-99(112)113/h8-14,22-25,27-28,52-55,61,64-76,80-81,131-132H,6-7,15-21,26,29-51,105H2,1-5H3,(H2,106,148)(H2,107,149)(H2,108,150)(H2,109,151)(H,133,153)(H,134,152)(H,135,154)(H,136,158)(H,137,162)(H,138,164)(H,139,161)(H,140,155)(H,141,165)(H,142,163)(H,143,156)(H,144,157)(H,145,166)(H,146,159)(H,147,160)(H4,110,111,124)(H4,112,113,125)(H4,114,115,126)(H4,116,117,127)(H4,118,119,128)(H4,120,121,129)(H4,122,123,130)/t54-,55-,61-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,80-,81-/m0/s1
InChI Key
IMPPEXHRQVNTSK-SSCHLACESA-N
Canonical SMILES
CCC(C)C(C(=O)NC(CCCNC(=N)N)C(=O)NC(C(C)CC)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC3=CC=CC=C3)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCSC)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(CCCNC(=N)N)N
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