Cyclisation of histidine containing peptides in the solid-phase by anchoring the imidazole ring to trityl resins

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 809-812

  Sabatino, Giuseppina ^a   Chelli, Mario ^a   Mazzucco, Silvia ^a   Ginanneschi, Mauro ^a   Papini, Anna Maria ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Cyclisation; Peptides; Piperazinones; Solid phase synthesis

Indexed keywords

HISTIDINE; PEPTIDE DERIVATIVE;

ARTICLE; CYCLIZATION; PEPTIDE ANALYSIS; PROTEIN ANALYSIS; PROTEIN STRUCTURE; STRUCTURE ANALYSIS;

EID: 0033593405     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02459-9     Document Type: Article

References (17)

1. Nishino, N.; Xu, M.; Mihara, H.; Fujimoto, T. Tetrahedron Lett. 1992, 33, 1479-1482.
2. Nishino, N.; Hayashida, J.; Arai, T.; Mihara, H.; Ueno, Y.; Kumagai, H. J. Chem. Soc., Perkin Trans. 1 1996, 939-946.
3. (a) Isied, S.S.; Kuehn, C.G.; Lyon, J.M.; Merrifield, R.B. J. Am. Chem. Soc. 1982, 104, 2632-2634;
4. (b) Rovero, P.; Quartara, L.; Fabbri, G. Tetrahedron Lett. 1991, 32, 2639-2642.
5. Abbreviations used: AcOH, acetic acid; Al, allyl; DCC, dicyclohexylcarbodiimide, DCM, dichloromethane; DIPEA, N,N-diisopropylethylamine; DMF, N,N-dimethylformamide; DVB, divinylbenzene; ESI-MS, electrospray ionization mass spectrometry; FAB-MS, fast atom bombardment mass spectrometry; Fmoc, 9-fluorenylmethoxycarbonyl; HATU, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo(4,5-b)pyridinium 1-hexafluorophosphate 3-oxide; MeOH, methanol; NMM, N-methylmorpholine; RP-HPLC, reversed-phase high performance liquid chromatography; r.t., room temperature; TBTU, 1-[bis(dimethylamino)methylene]-1H-benzotriazolium 1-tetrafluoroborate 3-oxide; tBu, tert-butyl; TFA, trifluoroacetic acid; Trt, trityl; Trt-®, trityl resin. Amino acid symbols denote the L configuration unless indicated otherwise.
6. (a) Albericio, F.; Barany, G.; Fields, G.B.; Hudson, D.; Kates, S.A.; Lyttle, M.H.; Solé, N.A. In Peptides 1992: Proceedings of the 22nd European Peptide Symposium Schneider, C.H.; Eberle, A.N. (Eds.), ESCOM Science Publishers, Leiden, The Netherlands, 1993, pp 191-192;
7. (b) Trzeciak, A.; Bannwarth, W. Tetrahedron Lett. 1992, 33, 4557-4560.
8. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Wenging, Y.; Schäfer, W. Tetrahedron Lett. 1989, 30, 3943-3946.
9. Kates, S.A; Solé, N.A.; Johnson, C.R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron Lett. 1993, 34, 1549-1552.
10. 2).
11. Fmoc-His(Trt-®)-OAl 3a was prepared as follows. Trityl chloride resin 2a from Novabiochem with a polymer matrix copoly(styrene-1% DVB) 200-400 mesh (0.95 mmol/g) was swelled in anhydrous DCM (10 mL/g resin). Then the resin was treated for 1 h with a solution of Fmoc-His-OAl 1 (2 eq) and DIPEA (4 eq) in DCM. It was then washed with DCM-MeOH-DIPEA (17 : 2 : 1), DCM, DMF, DCM, MeOH (2 x 10 mL/g resin each). Final resin substitution, 0.58 mmol/g [spectrophotometric determination of the loading by deprotection with piperidine-DMF (1 : 4) and measuring the absorbance of the adduct dibenzofulvenepiperidine at 301 nm].
12. 9 Final resin substitution, 0.105 mmol/g.
13. + 601 (FAB-MS).
14. Kaiser, E.; Colescott, R.L.; Bossinger, C.D.; Cook, P.I. Anal. Biochem. 1970, 34, 595-598.
15. + 583.5 (ESI-MS and FAB-MS).
16. Jensen, J.K.; Alsina, J.; Sogster, M.F.; Vàgner, J.; Albericio, F.; Barany, G. J. Am. Chem. Soc. 1998, 120, 5441-5452.
17. Del Fresno, M.; Alsina, J.; Royo, M.; Barany, G.; Albericio, F. Tetrahedron Lett. 1998, 39, 2639-2642.