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

Item No. 28138

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-alanyl-L-threonyl-L-lysyl-L-alanyl-L-alanyl-L-arginyl-L-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-prolylglycyl-L-lysine-biotin, trifluoroacetate salt
Synonyms
  • ATKAAR-K(Me3)-SAPATGGVKKPHRYRPG-K(Biotin)
  • H3(21-44)K27me3 Substrate
  • Histone H3 (21-44) (Lys27me3)
  • [Lys(Me3)27]-Histone H3 (21-44)-K(Biotin)
Molecular Formula
C128H217N43O32S • XCF3COOH
Formula Weight
2902.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
SMILES
O=C(CCCC[C@@H]1SC[C@@]([H])([C@@]1(N2)[H])NC2=O)NCCCC[C@H](NC(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[H])=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)C([O-])=O.O=C(O)C(F)(F)F
InChi Code
InChI=1S/C128H217N43O32S.C2HF3O2/c1-68(2)99(164-98(179)63-144-96(177)62-146-118(195)100(74(8)173)166-106(183)72(6)150-116(193)92-40-29-55-168(92)121(198)73(7)151-114(191)89(65-172)162-111(188)80(33-19-24-58-171(10,11)12)154-108(185)82(36-25-52-141-125(133)134)153-105(182)71(5)148-104(181)70(4)149-107(184)79(31-15-20-48-129)157-120(197)101(75(9)174)165-103(180)69(3)132)119(196)156-81(32-16-21-49-130)109(186)158-84(34-17-22-50-131)122(199)170-57-30-41-93(170)117(194)161-88(60-77-61-139-67-147-77)113(190)155-83(37-26-53-142-126(135)136)110(187)160-87(59-76-44-46-78(175)47-45-76)112(189)159-85(38-27-54-143-127(137)138)123(200)169-56-28-39-91(169)115(192)145-64-97(178)152-86(124(201)202)35-18-23-51-140-95(176)43-14-13-42-94-102-90(66-204-94)163-128(203)167-102;3-2(4,5)1(6)7/h44-47,61,67-75,79-94,99-102,172-174H,13-43,48-60,62-66,129-132H2,1-12H3,(H38-,133,134,135,136,137,138,139,140,141,142,143,144,145,146,147,148,149,150,151,152,153,154,155,156,157,158,159,160,161,162,163,164,165,166,167,175,176,177,178,179,180,181,182,183,184,185,186,187,188,189,190,191,192,193,194,195,196,197,201,202,203);(H,6,7)/t69-,70-,71-,72-,73-,74+,75+,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,99-,100-,101-,102-;/m0./s1
InChi Key
UETVEPGTQABIHB-BSARJIIZSA-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)-K-biotin is a peptide fragment of histone H3 that corresponds to amino acid residues 22-45 of the human histone H3.1 and H3.2 sequences. It is trimethylated at lysine 27 and biotinylated via a C-terminal lysine 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

    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).