Cell-penetrating Peptide Synthesis

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Cell-penetrating Peptide Synthesis

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Peptide synthesis: Cell Penetrating Peptide Oligonucleotide Conjugate

Amino acid sequences and properties of CPPs

Tat, the transcription activator of the human immunodeficiency virus type 1 (HIV-1) viral genome, enters cells in a non-toxic and highly efficient manner. Tat is the first known cell-penetrating peptide. More about pI, sequence, and structures of HS-binding cell penetrating peptides.

CPPs have been used as a carrier to deliver proteins or genes into cells and tissues. In this study, a CPP library composed of 55 CPPs were used to deliver genes into plant cells. Many CPPs showed efficient penetration into plant cells. The Lys-containing CPPs have higher penetration efficiency in the plant than in animal cells. This could be due to differences in lipid composition and surface charge of the cell membranes. No correlations were detected between the penetration efficiency and the cationic, amphipathic, or hydrophobic properties of peptides.

D-R9 is composed of D-form amino acids. D-R9 bound preferentially to the membrane and did not penetrate the cytosol or vacuole. In mammalian cells, poly-Lysine-based CPPs are efficient and interact with membrane lipid head groups to induce wrapping of the membrane monolayers. Arg-rich peptides, such as the Tat peptide, are among the most efficient CPPs. Arg-rich CPPs may generate negative Gaussian membrane curvature to form pores or protrusions from endocytosis. The cell penetration efficiency of CPPs containing poly-Arg is higher than those containing poly-Lys. However, in the plant, Arg-rich CPPs are not the most efficient at penetrating plant cell.

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Peptide No.CPPAmino acid sequenceNumber of amino acidsCPP type:
C: cationic, A: amphipathic, H: hydrophobic.
Net charge at pH7
1 BP100 KKLFKKILKYL 11 A 5
2 2BP100 KKLFKKILKY LKKLFKKILK YL 22 C 10
3 Rev(34–50) TRQARRNRRR RWRERQR 17 C 9
4 R9 RRRRRRRRR 9 C 9
5 D-R9 rrrrrrrrr (D form) 9 C 9
6 R12 RRRRR RRRRR RR 12 C 12
7 KH9 KHKHKHKHKH KHKHKHKH 18 C 9.9
8 K9 KKKKKKKKK 9 C 9
9 K18 KKKKK KKKKK KKKKK KKK 18 C 18
10 Pen2W2F RQIKI FFQNR RMKFKK 16 C 7
11 DPV3 RKKRR RESRK KRRRES 16 C 10
12 6-Oct GRKRKKRT 8 C 6
13 R9-TAT GRRRR RRRRR PPQ 13 C 9
14 Tat(49–57) RKKRRQRRR 9 C 8
15 Retro - Tat(57–49) RRRQRRKKR 9 C 8
16 Sc18 GLRKRLRKFR NKIKEK 16 A 8
17 KLA10 KALKKLLAKW LAAAKALL 18 A 5
18 IX QLALQLALQA LQAALQLA 18 H 0
19 XI LKTLATALTK LAKTLTTL 18 H 3
20 No. 14–12 RAWMRWYSPT TRRYG 15 A 4
21 pVEC LLIILRRRIR KQAHAHSK 18 A 6.2
22 PenArg RQIRIWFQNR RMRWRR 16 A 7
23 M918 MVTVLFRRLR IRRACGPPRV RV 22 A 6.9
24 Penetratin RQIKI WFQNR RMKWK K 16 A 7
25 PolyP 3 (SAP) VRLPP PVRLP PPVRL PPP 18 H 3
26 dhvar5 LLLFL LKKRK KRKY 14 A 7
27 HPV33L2-445/467 SYFIL RRRRK RFPYF FTDVR VAA 23 A 6
28 buforin II (5–21) RAGLQ FPVGR VHRLL RK 17 A 5.1
29 scrambled pVEC IAARI KLRSR QHIKL RHL 18 A 6.2
30 HPV33L2-DD447 SYDDL RRRRK RFPYF FTDVR VAA 23 A 4
31 LAH4 KKALL ALALH HLAHL ALHLA LALKKA 26 H 4.4
32 ppTG1 GLFKA LLKLL KSLWK LLLKA 20 A 5
33 Transportan (TP) GWTLN SAGYL LGKIN LKALA ALAKK IL 27 H 4
34 2×ppTG1 GLFKA LLKLL KSLWK LLLKA GLFKA LLKLL KSLWKLLLKA 40 A 10
35 pAntpHD(Pro50) RQIKI WFPNR RMKWKK 16 A 7
36 pAntp(44–58) QIKIW FQNRR MKWKK 15 A 6
37 Crot(27–39) KMDCR WRWKC CKK 13 A 4.8
38 Crot(27–39) derevative (1) MDCRW RWKCC KK 12 A 3.8
39 Crot(27–39) derevative (2) KCGCR WRWKC GCKK 14 A 5.7
40 CyLoP-1 CRWRW KCCKK 10 A 4.8
41 Inv3 TKRRI TPKDV IDVRS VTTEI NT 22 H 2
42 Inv5 AEKVD PVKLN LTLSA AAEAL TGLGD K 26 H -1
43 Inv3.5 TKRRI TPKDV IDVRS VTTKI NT 22 H 4
44 Inv3.10 HHHHHH TKRRITPK DVIDVRSVTTEINT 28 H 2.6
45 ARF(1–22) MVRRF LVTLR IRRAC GPPRV RV 22 A 6.9
46 Cyt C 77–101 GTKMI FVGIK KKEER ADLIA YLKKA 25 A 4
47 hLF peptide KCFQWQRNM RKVRGPPVSCIKR 22 A 6.9
48 Glu-Oct-6 EEEAA GRKRKKRT 13 A 3
49 M511 FLGKK FKKYF LQLLK 15 A 5
50 G53-4 FLIFI RVICI VIAKL KANLM CKT 23 H 3.9
51 M591 YIVLR RRRKR VNTKRS 16 A 8
52 E162 KTVLL RKLLK LLVRKI 16 A 6
53 E165 LLKKR KVVRL IKFLLK 16 A 7
54 M867 KKICT RKPRF MSAWAQ 16 A 4.9
55 MG2d GIGKFLHSAKK WGKAFVGQIMNC 23 H 4
56 Antitrypsin (358-374) CSIPP EVKFN KPFVYLI 17 H 0.9
57 BAC715-24 PRPLPFPRPG 10 A 2
58 BMV Gag-(7-25) KMTRA QRRAA ARRNR WTAR 19 C 8
59 BUFORIN II TRSSR AGLQF PVGRV HRLLRK 21 A 6.1
60 CADY Ac-GLWRA LWRLL RSLWR LLWRA-cysteamide 21 H 4
61 CCMV Gag-(7-25) KLRTR AQRRA AARKN KRNTR 20 C 10
62 ARF Peptide (26-44) H-D-Arg-D-Arg-D-Arg-D-Arg-D-Arg -D-Arg-D-Arg-D-Arg-D-Arg-Lys -Phe-Val-Arg-Arg-Ser -Arg-Arg-Pro-Arg-Thr- Ala-Ser-Cys-Ala-Leu- Ala-Phe-Val-Asn-OH 29 A 14.9
63 FHV COAT-(35-49) RRRRN RTRRN RRRVR 15 C 11
64 Calcitonin LGTYT QDFNK FHTFP QTAIG VGAP 24 H 0.1
65 HN-1 TSPLNIHNGQKL 12 H 1.1
66 HTLV-II Rex-(4-16) TRRQRTRRARRNR 13 C 8
67 Human P: MGLGL HLLVL AAALQ GAWSQ PKKKRKV 27 H 5.1
68 Human P MGLGL HLLVL AAALQ GAWSQ PKKKRKV 27 H 5.1
69 K-FGF AAVAL LPAVL LALLAP 16 H 0
70 Ku70 VPMLKPMLKE 10 A 1
71 MAP KLALKLALHA LKAALKLAKL ALKLALKALK AALKLA-NH2 36 H 10.1
72 Maurocalcine GDC(acm)LP HLKLC 10 H 0
73 Neurturin GAAEA AARVY DLGLR RLRQR RRLRR ERVRA 30 A 8

Other examples are:

  • Antennapedia (43-58):RQIKIWFQNRRMKWKK;
  • Antitrypsin (358-374): CSIPPEVKFNKPFVYLI;
  • BAC715-24: PRPLPFPRPG;
  • BMV Gag-(7-25): KMTRAQRR AAARRNRWTAR;
  • BUFORIN II: TRSSRAGLQF PVGRVHRLLRK;
  • CADY: Ac-GLWRALWRLLR SLWRLLWRA-cysteamide;
  • CCMV Gag-(7-25): KLRTRAQRRAAARKNKRNTR;
  • ARF Peptide (26-44): H-D-Arg-D-Arg-D-Arg-D-Arg-D-Arg-D-Arg -D-Arg-D-Arg-D-Arg-Lys-Phe-Val-Arg-Arg-Ser-Arg -Arg-Pro-Arg-Thr-Ala-Ser-Cys-Ala-Leu-Ala-Phe-Val-Asn-OH
  • D-TAT: Grkkrrqrrrppq-NH2;
  • FHV COAT-(35-49): RRRRNRT RRNRRRVR;
  • hCT (9-32) Calcitonin: LGTYTQDFNKF HTFPQTAIGVGAP;
  • HIV-1 Rev (34-50): TRQARRNRR RRWRERQR;
  • HN-1: TSPLNIHNGQKL;
  • HTLV-II Rex-(4-16): TRRQRTRRARRNR;
  • Human P1: MGLGLHLLVLAA ALQGAWSQPKKKRKV;
  • K-FGF: AAVALLPAVLLALLAP;
  • Ku70: VPMLKPMLKE;
  • MAP: KLALKLALHALKAALKLAKL ALKLALKALKAALKLA-NH2;
  • Maurocalcine: GDC(acm)LPHLKLC;
  • MPG: Ac-GALFLAFLAAALSLMGLWSQPKKKRRV-Cya; Cysteamide or Cya (-NH-CH2-CH2-SH)
  • MPG(ΔNLS): Ac-GALFLGFLGAAGS TMGAWSQPKKKRKV-Cya; Cysteamide or Cya (-NH-CH2-CH2-SH)
  • Neurturin: GAAEAAARVYDLGL RRLRQRRRLRRERVRA;
  • P22 N-(14-30): NAKTRRHERRRKLAIER;
  • Pen2W2F: Fluo-RQIKIFFQNRRMKFKK-NH2;
  • Penetratin-Arg: RQIRIWFQNRRMRWRR;
  • Penetratin: RQIKIWFQNRRMKWKKGG;
  • Pep-1: Ac-KETWWETWWTEWSQPKKKRKV-Cys;
  • Pep-2: Ac-KETWFETWFTEWSQPKKKRKV-Cys;
  • Pep-7: SDLWEMMMVSLACQY;
  • plsl-1: RVIRVWFQNKRCKDKK;
  • pVEC (Cadherin-5): LLIILRRRIRKQAHAHSK;
  • R7W: Fluo-RRRRRRRW-NH2;
  • RVG-9R: YTIWMPENPRPGTP CDIFTNSRGKRASN GGGGRRRRRRRRR;
  • SAP: VRLPPPVRLPPPVRLPPP;
  • SV-40 Large T-antigen Nuclear Localization Signal:CGGGPKKKRKVED;
  • SynB1: RGGRLSYSRRRFSTSTGR;
  • SynB3: RRLSYSRRRF;
  • HIV-1 Tat (48-60):GRKKRRQRRRPPQ;
  • TAT (HIV-1 (48-61)): GRKKRRQRRRPPQQ;
  • TAT (HIV-1 (49-57)): RKKRRQRRR;
  • TAT (47-57): YGRKKRRQRRR;
  • TAT R9: GRRRRRRRRRPPQ;
  • TAT P59W: Fluo-GRKKRRQRRRPWQ-NH2;
  • TAT-HA2 Fusion Peptide: RRRQRRKKRGGD IMGEWGNEIFGAIAGFLG;
  • Temporin L: FVQWFSKFLGRIL-NH2;
  • Transportan: GWTLNSAGYLLGKINLKALAALAKKIL;
  • VP-22: DAATATRGRSAASRPTE RPRAPARSASRPRRPVD;
  • PTD-4: PIRRRKKLRRLK;
  • PTD-5: RRQRRTSKLMKR;
  • SBP: MGLGLHLLVLAAALQGAWSQPKKKRKV;
  • FBP: GALFLGWLGAAGSTMGAWSQPKKKRKV;

Download the full list HERE!

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