Synthesis of an RNA-peptide conjugate by orthogonal ligation

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 978-980

  McPherson, Michael ^a   Wright, Martin C ^a   Lohse, Peter A ^a  

^a Phylos Inc   (United States)

Author keywords

Encoded peptide library; Nucleic acid protein conjugate; Orthogonal ligation; RNA peptide conjugate

Indexed keywords

NUCLEIC ACID; PEPTIDE; PROTEIN; RNA;

ARTICLE; CHEMICAL REACTION; CONJUGATION; PEPTIDE SYNTHESIS; PROTEIN RNA BINDING; PROTEIN SYNTHESIS; REACTION ANALYSIS; RNA SYNTHESIS;

EID: 0032976769     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3107     Document Type: Article

References (47)

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11. Peyrottes, S.; Mestre, B.; Burlina, F.; Gait, M. J. Tetrahedron 1998, 54, 12513. Jungmann, V.; Waldmann, H. Tetrahedron Lett. 1998, 39, 1139. Waldmann, H.; Gabold, S. J. Chem. Soc., Chem. Commun. 1997, 19, 1861. Robles, J.; Pedroso, E.; Grandas, A. J. Org. Chem. 1994, 59, 2482. Robles, J.; Pedroso, E.; Grandas, A. Tetrahedron Lett. 1994, 35, 4449. Dreef-Tromp, C. M.; van den Elst, H.; van den Boogaart, J. E.; van der Marel, G. A.; van Boom, J. H. Nucleic Acids Res. 1992, 20, 2435. Dreef-Tromp, C. M.; van der Maarel, J. C. M.; van den Elst, H.; van der Marel, G. A.; van Boom, J. H. Nucleic Acids Res. 1992, 20, 4015. Kuyl-Yeheskiely, E.; Tromp, C. M.; Lefeber, A. W. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1988, 44, 6515. Juodka, B. A. Nucleosides Nucleotides 1984, 3, 445,
12. Peyrottes, S.; Mestre, B.; Burlina, F.; Gait, M. J. Tetrahedron 1998, 54, 12513. Jungmann, V.; Waldmann, H. Tetrahedron Lett. 1998, 39, 1139. Waldmann, H.; Gabold, S. J. Chem. Soc., Chem. Commun. 1997, 19, 1861. Robles, J.; Pedroso, E.; Grandas, A. J. Org. Chem. 1994, 59, 2482. Robles, J.; Pedroso, E.; Grandas, A. Tetrahedron Lett. 1994, 35, 4449. Dreef-Tromp, C. M.; van den Elst, H.; van den Boogaart, J. E.; van der Marel, G. A.; van Boom, J. H. Nucleic Acids Res. 1992, 20, 2435. Dreef-Tromp, C. M.; van der Maarel, J. C. M.; van den Elst, H.; van der Marel, G. A.; van Boom, J. H. Nucleic Acids Res. 1992, 20, 4015. Kuyl-Yeheskiely, E.; Tromp, C. M.; Lefeber, A. W. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1988, 44, 6515. Juodka, B. A. Nucleosides Nucleotides 1984, 3, 445,
13. Peyrottes, S.; Mestre, B.; Burlina, F.; Gait, M. J. Tetrahedron 1998, 54, 12513. Jungmann, V.; Waldmann, H. Tetrahedron Lett. 1998, 39, 1139. Waldmann, H.; Gabold, S. J. Chem. Soc., Chem. Commun. 1997, 19, 1861. Robles, J.; Pedroso, E.; Grandas, A. J. Org. Chem. 1994, 59, 2482. Robles, J.; Pedroso, E.; Grandas, A. Tetrahedron Lett. 1994, 35, 4449. Dreef-Tromp, C. M.; van den Elst, H.; van den Boogaart, J. E.; van der Marel, G. A.; van Boom, J. H. Nucleic Acids Res. 1992, 20, 2435. Dreef-Tromp, C. M.; van der Maarel, J. C. M.; van den Elst, H.; van der Marel, G. A.; van Boom, J. H. Nucleic Acids Res. 1992, 20, 4015. Kuyl-Yeheskiely, E.; Tromp, C. M.; Lefeber, A. W. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1988, 44, 6515. Juodka, B. A. Nucleosides Nucleotides 1984, 3, 445,
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34. + salt 1 (5 mg, 12 μmol, United States Biochemical Corporation) in deionized water (1,5 ml), was added phenyl α-bromo-thioacetate 2 (26 mg, 0.11 mmol, 10 equiv) in DMSO (0.5ml) and the reaction was stirred at room temperature for 5 min. The reaction mixture was extracted with diethyl ether (3 × 1.5 ml) to recover unreacted 2 and the resulting solution of GMPS thioester 3 was of sufficient purity (95 % by RP-HPLC) to be used in the next step. HPLC (Brownlee Spheri 5 RP18 column, 22 cm × 4.6 mm; Perkin Elmer): elution with 3 % acetonitrile in 0.1 M triethylammonium acetate (pH 7) for 10 min, followed by a linear gradient of 3% to 100% acetonitrile over 10 min, followed by a 5 min wash at 100% acetonitrile; flow rate 1 ml/min, detection at 260 nm, Rt = 5.4 min (1), Rt = 14.8 min (3).
35. 4) δ 18.9; MS (ES neg.) m/z 528.0 (M-1).
36. To a solution of 3 (12 μmol) in deionized water (1.5 ml) was added Cys-Gly (2.1 mg, 12 μmol) and the reaction was left to stir at room temperature for 1 h. Lyophilization of the reaction mixture gave the product 4 in 95 % yield. HPLC conditions, see reference 12.
37. 4) δ 19.60; MS (ES neg.) m/z 596.2 (M-1).
38. 32P-labeled RNA (102mer) was purified by polyacrylamide gel electrophoresis and derivatized: RNA (1 μM) was reacted with phenyl α-bromothioacetate 2 (10 mM, DMSO solution) in 100 μl sodium phosphate (10 mM, pH 6.8) for 40 min at room temperature. The solution was extracted twice with chloroform to remove the excess unreacted bromide 2 and the resulting 5'-alkylated RNA was used immediately.
39. 32P-labeled RNA.
40. 32P-label. No binding was observed when peptidc B was used, but peptide A resulted in 30 % of the RNA being retained on the beads.
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