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ZIP acetate

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ZIP acetate is a cell-permeable inhibitor of protein kinase Mζ (PKMζ), which is a constitutively active and atypical PKC isozyme involved in LTP maintenance. ZIP selectively blocks PKMζ-induced synaptic potentiation in hippocampal slices in vitro. ZIP reverses late-phase LTP (IC50 = 1-2.5 μM) and produces persistent loss of 1-day-old spatial memory following central administration in vivo.

Category

Functional Peptides

Catalog number

BAT-016387

Molecular Formula

C92H158N30O19

Molecular Weight

1988.43

Specification

IUPAC Name

acetic acid;(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-5-carbamimidamido-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-carbamimidamido-2-(tetradecanoylamino)pentanoyl]amino]-4-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]pentanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]acetyl]amino]-5-carbamimidamidopentanoic acid

Synonyms

myristoyl-Arg-Leu-Tyr-Arg-Lys-Arg-Ile-Trp-Arg-Ser-Ala-Gly-Arg-OH.CH3CO2H; N-myristoyl-L-arginyl-L-leucyl-L-tyrosyl-L-arginyl-L-lysyl-L-arginyl-L-isoleucyl-L-tryptophyl-L-arginyl-L-seryl-L-alanyl-glycyl-L-arginine acetic acid; N-(1-Oxotetradecyl)-L-seryl-L-isoleucyl-L-tyrosyl-L-arginyl-L-arginylglycyl-L-alanyl-L-arginyl-L-arginyl-L-tryptophyl-L-arginyl-L-lysyl-L-leucine acetate; Peptide ZIP acetate; z-Pseudosubstrate inhibitory peptide acetate

Related CAS

863987-12-6 (free base)

Purity

≥94%

Sequence

Myr-RLYRKRIWRSAGR.CH3CO2H

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C90H154N30O17.C2H4O2/c1-7-9-10-11-12-13-14-15-16-17-18-36-71(123)110-61(31-23-42-102-86(92)93)75(126)116-67(47-53(3)4)80(131)117-68(48-56-37-39-58(122)40-38-56)81(132)114-63(32-24-43-103-87(94)95)77(128)112-62(30-21-22-41-91)76(127)113-65(34-26-45-105-89(98)99)79(130)120-73(54(5)8-2)84(135)118-69(49-57-50-107-60-29-20-19-28-59(57)60)82(133)115-64(33-25-44-104-88(96)97)78(129)119-70(52-121)83(134)109-55(6)74(125)108-51-72(124)111-66(85(136)137)35-27-46-106-90(100)101;1-2(3)4/h19-20,28-29,37-40,50,53-55,61-70,73,107,121-122H,7-18,21-27,30-36,41-49,51-52,91H2,1-6H3,(H,108,125)(H,109,134)(H,110,123)(H,111,124)(H,112,128)(H,113,127)(H,114,132)(H,115,133)(H,116,126)(H,117,131)(H,118,135)(H,119,129)(H,120,130)(H,136,137)(H4,92,93,102)(H4,94,95,103)(H4,96,97,104)(H4,98,99,105)(H4,100,101,106);1H3,(H,3,4)/t54-,55-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,73-;/m0./s1

InChI Key

AFOAEBCWCHNSMC-CQUAHXNOSA-N

Canonical SMILES

CCCCCCCCCCCCCC(=O)NC(CCCNC(=N)N)C(=O)NC(CC(C)C)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CCCNC(=N)N)C(=O)NC(C(C)CC)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)NC(CCCNC(=N)N)C(=O)NC(CO)C(=O)NC(C)C(=O)NCC(=O)NC(CCCNC(=N)N)C(=O)O.CC(=O)O