Use of the dithiasuccinoyl (Dts) amino protecting group for solid-phase synthesis of protected peptide nucleic acid (PNA) oligomers

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7281-7289

  Planas, Marta ^a,b   Bardají, Eduard ^a,b   Jensen, Knud J ^a,c   Barany, George ^a  

^a University of Minnesota   (United States)

^b UNIVERSITY OF GIRONA   (Spain)

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMER; PEPTIDE NUCLEIC ACID; PROTECTIVE AGENT;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; MASS SPECTROMETRY; SOLID STATE; SYNTHESIS;

EID: 0033214142     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9824394     Document Type: Article

References (60)

1. Preliminary accounts of this work have been reported. (a) Working only with Dts-T-OH: Jensen, K. J.; Bardají, E.; Albericio, F.; Coull, J. M.; Barany, G. In Peptides 1994: Proceedings of the Twenty-Third European Peptide Symposium; Braga, Portugal, Sep 4-10, 1994; Maia, H. L. S., Ed.; ESCOM Science Publishers: Leiden, The Netherlands, 1995; pp 757-758. (b) Planas, M.; Bardaji; Barany, G. In Peptides 1998: Proceedings of the Twenty-Fifth European Peptide Symposium; Budapest, Hungary, Aug 30-Sep 4, 1998; Bajusz, S., Hudecz, F., Eds.; Akadémia Kiadó: Budapest, Hungary, 1999; pp 234- 235.
2. Preliminary accounts of this work have been reported. (a) Working only with Dts-T-OH: Jensen, K. J.; Bardají, E.; Albericio, F.; Coull, J. M.; Barany, G. In Peptides 1994: Proceedings of the Twenty- Third European Peptide Symposium; Braga, Portugal, Sep 4-10, 1994; Maia, H. L. S., Ed.; ESCOM Science Publishers: Leiden, The Netherlands, 1995; pp 757-758. (b) Planas, M.; Bardaji; Barany, G. In Peptides 1998: Proceedings of the Twenty-Fifth European Peptide Symposium; Budapest, Hungary, Aug 30-Sep 4, 1998; Bajusz, S., Hudecz, F., Eds.; Akadémia Kiadó: Budapest, Hungary, 1999; pp 234-235.
3. 2O, diethyl ether; EtOAc, ethyl acetate; EtOH, ethanol; FABMS, fast-atom bombardment mass spectrometry; Fmoc, 9-fluorenylmethoxycarbonyl; HAL, 5-(4-hydroxymethyl-3,5-dimethoxyphenoxy) valeric acid handle; HATU, N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N- methylmethanamimum hexafluorophosphate N-oxide; HBTU, N-[1H-(benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; HOAc, acetic acid; HOAt, 7-aza-1-hydroxybenzotriazole (3-hydroxy-3H-1,2,3-triazolo-[4,5-b]pyridine); HOBt, 1-hydroxybenzotriazole; HPLC, high-performance liquid chromatography; IRAA, "internal reference" amino acid; MAc, N-methylmercaptoacetamide; MSNT, 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole; NMM, N-methylmorpholine; NMP, N-methyl-2-pyrrolidinone; PAL, 5-[[(4-amino)-methyl]-3,5-dimethoxyphenoxy]valeric acid handle (Peptide Amide Linker); PEG-PS, poly(ethylene glyco)-polystyrene (graft resin support); TBTU, O-(benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; TFA, trifluoroacetic acid; TFFH, 1,1,3,3-tetramethyl 2-fluoroformamidinium hexafluorophosphate; Z, benzyloxycarbonyl. All solvent ratios are volume/volume unless stated otherwise.
4. 2 is the C-terminal glycinamide; Dts denotes the N-terminal amino protecting group; and, Z is the N-amino protecting group of the nucleobases. We also point out that while technically PNA molecules are neutral rather than acidic, workers in the field have retained the term "acid" in the name to emphasize the analogy to DNA and RNA.
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8. Reviews: (a) Nielsen, P. E. Methods Enzymol. 1996, 267, 426- 433. (b) Hyrup, B.; Nielsen, P. E. Bioorg. Biomed. Chem. 1996, 4, 5-23. (c) M. Eriksson, M.; Nielsen, P. E. Quart. Rev. Biophys. 1996, 29, 369-394. (d) Good, L.; Nielsen, P. E. Antisense and Nucleic Acid Drug Dev. 1997, 7, 431-437. (e) Knudsen, H.; Nielsen, P. E. Anti-Cancer Drugs 1997, 8, 113-118. (f) Duehohn, K. L.; Nielsen, P. E. New J. Chem. 1997, 21, 19-31. (g) Haaima, G.; Nielsen, P. E. Chem. Soc. Rev. 1997, 73-78. (h) Corey, D. R. TIBTECH 1997, 15, 224-229.
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12. Reviews: (a) Nielsen, P. E. Methods Enzymol. 1996, 267, 426- 433. (b) Hyrup, B.; Nielsen, P. E. Bioorg. Biomed. Chem. 1996, 4, 5-23. (c) M. Eriksson, M.; Nielsen, P. E. Quart. Rev. Biophys. 1996, 29, 369- 394. (d) Good, L.; Nielsen, P. E. Antisense and Nucleic Acid Drug Dev. 1997, 7, 431-437. (e) Knudsen, H.; Nielsen, P. E. Anti-Cancer Drugs 1997, 8, 113-118. (f) Duehohn, K. L.; Nielsen, P. E. New J. Chem. 1997, 21, 19-31. (g) Haaima, G.; Nielsen, P. E. Chem. Soc. Rev. 1997, 73-78. (h) Corey, D. R. TIBTECH 1997, 15, 224-229.
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