A biotinylated peptide fragment of histone H3
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Histone H3K27Me3 (21-44)-GK-biotin (trifluoroacetate salt)

Item No. 27767

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-alanyl-L-threonyl-L-lysyl-L-alanyl-L-alanyl-L-arginyl-6-(trimethylammonio)-L-norleucyl-L-seryl-L-alanyl-L-prolyl-L-alanyl-L-threonylglycylglycyl-L-valyl-L-lysyl-L-lysyl-L-prolyl-L-histidyl-L-arginyl-L-tyrosyl-L-arginyl-L-prolylglycylglycyl-L-lysine-biotin, trifluoroacetate salt
Synonyms
  • ATKAAR-K(Me3)-SAPATGGVKKPHRYRPG-GK(Biotin)
  • H3(21-44)K27me3 Substrate
  • Histone H3 (21-44) (Lys27me3)
  • [Lys(Me3)27]-Histone H3 (21-44)-GK(Biotin)
Molecular Formula
C130H220N44O33S • XCF3COOH
Formula Weight
2959.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
SMILES
O=C(O)C(F)(F)F.O=C(CCCC[C@@H]1SC[C@@]([H])([C@@]1(N2)[H])NC2=O)NCCCC[C@H](NC(CNC(CNC([C@@H]3CCCN3C([C@@H](NC([C@H](CC4=CC=C(C=C4)O)NC([C@@H](NC([C@H](CC5=CN=CN5)NC([C@@H]6CCCN6C([C@@H](NC([C@@H](NC([C@@H](NC(CNC(CNC([C@@]([H])(NC([C@H](C)NC([C@@H]7CCCN7C([C@H](C)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](C)NC([C@H](C)NC([C@@H](NC([C@@]([H])(NC([C@H](C)N)=O)[C@H](O)C)=O)CCCCN)=O)=O)=O)CCCNC(N)=N)=O)CCCC[N+](C)(C)C)=O)CO)=O)=O)=O)=O)[C@H](O)C)=O)=O)=O)C(C)C)=O)CCCCN)=O)CCCCN)=O)=O)=O)CCCNC(N)=N)=O)=O)CCCNC(N)=N)=O)=O)=O)=O)C([O-])=O
InChi Code
InChI=1S/C130H220N44O33S.C2HF3O2/c1-69(2)101(167-100(183)65-147-98(181)63-149-120(199)102(75(8)176)169-108(187)73(6)153-118(197)93-40-29-55-171(93)123(202)74(7)154-116(195)90(66-175)165-113(192)81(33-19-24-58-174(10,11)12)157-110(189)83(36-25-52-143-127(135)136)156-107(186)72(5)151-106(185)71(4)152-109(188)80(31-15-20-48-131)160-122(201)103(76(9)177)168-105(184)70(3)134)121(200)159-82(32-16-21-49-132)111(190)161-85(34-17-22-50-133)124(203)173-57-30-41-94(173)119(198)164-89(60-78-61-141-68-150-78)115(194)158-84(37-26-53-144-128(137)138)112(191)163-88(59-77-44-46-79(178)47-45-77)114(193)162-86(38-27-54-145-129(139)140)125(204)172-56-28-39-92(172)117(196)148-62-97(180)146-64-99(182)155-87(126(205)206)35-18-23-51-142-96(179)43-14-13-42-95-104-91(67-208-95)166-130(207)170-104;3-2(4,5)1(6)7/h44-47,61,68-76,80-95,101-104,175-177H,13-43,48-60,62-67,131-134H2,1-12H3,(H39-,135,136,137,138,139,140,141,142,143,144,145,146,147,148,149,150,151,152,153,154,155,156,157,158,159,160,161,162,163,164,165,166,167,168,169,170,178,179,180,181,182,183,184,185,186,187,188,189,190,191,192,193,194,195,196,197,198,199,200,201,205,206,207);(H,6,7)/t70-,71-,72-,73-,74-,75+,76+,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,101-,102-,103-,104-;/m0./s1
InChi Key
HYQUUKCXSSEIJL-OYLSTRRTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Histone H3K27Me3 (21-44)-GK-biotin is a peptide fragment of histone H3 that corresponds to amino acid residues 22-45 of the human histone H3.1 and 3.2 sequences. It is trimethylated at lysine 27 and biotinylated via a C-terminal GK linker. Trimethylation of histone H3 at lysine 27 is associated with gene silencing.1 It is involved in tumor progression through its regulation by enhancer of zeste homolog 2 (EZH2) and transcriptional repression of tumor suppressor genes.2,3 Levels of H3K27Me3 are reduced in 293 T-REx cells containing EEDR236T and SUZ12G610V mutations and in lymphoblastoid cells isolated from patients with Weaver syndrome, a rare overgrowth disorder characterized by EZH2, EED, or SUZ12 mutations, cancer susceptibility, and various distinctive physical features.4 Histone H3K27Me3 (21-44)-GK-biotin has been used as a substrate for histone lysine demethylases (KDMs) to determine substrate specificity.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Becker, J.S., Nicetto, D., and Zaret, K.S. H3K9me3-dependent heterochromatin: Barrier to cell fate changes. Trends Genet. 32(1), 29-41 (2016).

    2. Wu, Z., Lee, S.T., Qiao, Y., et al. Polycomb protein EZH2 regulates cancer cell fate decision in response to DNA damage. Cell Death Differ. 18(11), 1771-1779 (2011).

    3. Gan, L., Yang, Y., Li, Q., et al. Epigenetic regulation of cancer progression by EZH2: From biological insights to therapeutic potential. Biomark. Res. 6, 10 (2018).

    4. Imagawa, E., Higashimoto, K., Sakai, Y., et al. Mutations in genes encoding polycomb repressive complex 2 subunits cause Weaver syndrome. Hum. Mutat. 38(6), 637-648 (2017).

    5. Laukka, T., Myllykoshi, M., Looper, R.E., et al. Cancer-associated 2-oxoglutarate analogues modify histone methylation by inhibiting histone lysine demethylases. J. Mol. Biol. 430(18 pt B), 3081-3092 (2018).