Solid-phase synthesis: A linker for side-chain anchoring of arginine

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5319-5321

  García, Oscar ^a   Nicolás, Ernesto ^a   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Benzofuran; Benzopyran; Combinatorial chemistry; Handle; Linker; Protecting group; Solid phase

Indexed keywords

ARGININE; CHROMAN DERIVATIVE; GUANIDINE; SCAVENGER;

AMINO ACID ANALYSIS; ARTICLE; CATALYSIS; ELECTRON TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; REDUCTION; SOLID; SYNTHESIS;

LETHRINIDAE;

EID: 0038684450     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01203-6     Document Type: Article

References (24)

1. Blackburn C., Albericio F., Kates S.A. Drugs Future. 22:1997;1007-1025.
2. Blackburn C. Kates S.A., Albericio F. Solid-Phase Synthesis. A Practical Guide. 2000;197-273 Marcel Dekker, New York.
3. Guillier F., Orain D., Bradley M. Chem. Rev. 100:2000;2091-2157.
4. Bannwarth W. Methods Principles Med. Chem. 9:2000;47-98.
5. Albericio F., Giralt E. Goodman M., Felix A., Moroder L., Toniolo C. Houben-Weyl. Methods of Organic Chemistry. Vol. E 22: Synthesis of Peptides and Peptidomimetics. 2001;685-709 Georg Thieme, Stuttgart.
6. Songster M.F., Barany G. Methods Enzym. 289:1997;126-174.
7. Thamm P., Kolbeck W., Musiol H.J., Moroder L. Goodman M., Felix A., Moroder L., Toniolo C. Houben-Weyl. Methods of Organic Chemistry. Vol. E 22: Synthesis of Peptides and Peptidomimetics. 2001;315-333 Georg Thieme, Stuttgart.
8. Fmoc-Arg(Trt)-OH has also been described (Caciagli, V., Verdini, A. S. In Peptide Chemistry 1987; Shiba, T.; Sakakibara, S., Eds.; Protein Research Foundation: Osaka, Japan, 1998; pp. 283), but its poor solubility in the solvents generally employed in SPPS has precluded its use in peptide synthesis. On the other hand, the 5H-dibenzo[a,d]cycloheptene-based groups (Noda, M.; Kiffe, M. J. Peptide Res. 1997, 50, 329-335) appear to be more promising for use in SPPS.
9. Fmoc-Arg(Trt)-OH has also been described (Caciagli, V., Verdini, A. S. In Peptide Chemistry 1987; Shiba, T.; Sakakibara, S., Eds.; Protein Research Foundation: Osaka, Japan, 1998; pp. 283), but its poor solubility in the solvents generally employed in SPPS has precluded its use in peptide synthesis. On the other hand, the 5H-dibenzo[a,d]cycloheptene-based groups (Noda, M.; Kiffe, M. J. Peptide Res. 1997, 50, 329-335) appear to be more promising for use in SPPS.
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12. 2NH, diethylamine; Fmoc, 9-fluorenylmethoxycarbonyl; HOBt, 1-hydroxybenzotriazole; TFA, trifluoroacetic acid. Amino acid symbols denote the L-configuration.
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16. García, O.; Nicolás, E.; Albericio, F. Tetrahedron Lett., submitted for publication.
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19. The use of large excesses of diethyl isopropyldenemalonate (16 equiv.) led to clear improvements in the yield.
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22. Fmoc-Arg-OAllyl was prepared by reaction of Fmoc-Arg-OH with neat allyl alcohol in the presence of p-toluenesulfonic acid in a round-bottomed flask equipped with a Dean-Stark apparatus at 100°C for 30 min. Toluene was then added and the mixture was heated under reflux for 3 h. The product was obtained after work-up and crystallization (82% yield).
23. Handbook of Synthetic Substrates for the Coagulation and Fibrinolytic System; Hemker, H. C., Ed.; Martinus Nijhof Publishers: Boston, USA, 1983.
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