Abstract
SynPhase lanterns and microwave irradiation have been combined to set up an efficient and rapid cyclization strategy of short peptides.
Key words
SynPhase lanterns - microwave - cyclization - cyclic peptides
References and Notes
1a Davidson BS.
Chem. Rev.
1993,
93:
1771
1b Fusetani N.
Matsunaga S.
Chem. Rev.
1993,
93:
1793
1c De Lucca AJ.
Walsh TJ.
Rev. Iberoam. Micol.
2000,
17:
116
1d Aneiros A.
Garateix A.
J. Chromatogr. B
2004,
803:
41
2a Toniolo C.
Int. J. Pept. Protein Res.
1990,
35:
287
2b Fairlie DP.
Abbenante G.
March DR.
Curr. Med. Chem.
1995,
2:
654
2c Cowell SM.
Lee YS.
Cain JP.
Hruby VJ.
Curr. Med. Chem.
2004,
11:
2785
3a Wipf P.
Chem. Rev.
1995,
95:
2115
3b Humphrey JM.
Chamberlin AR.
Chem. Rev.
1997,
97:
2243
3c Lambert JN.
Mitchell JP.
Roberts KD.
J. Chem. Soc., Perkin Trans. 1
2001,
471
3d Horton DA.
Bourne GT.
Smythe ML.
J. Comput. Aided Mol. Des.
2002,
16:
415
3e Davies JS.
J. Peptide Sci.
2003,
9:
471
3f Alcaro MC.
Sabatino G.
Uziel J.
Chelli M.
Ginanneschi M.
Rovero P.
Papini AM.
J. Pept. Sci.
2004,
10:
218
4a Planas M.
Bardají E.
Barany G.
Tetrahedron Lett.
2000,
41:
4097
4b Cros E.
Planas M.
Barany G.
Bardají E.
Eur. J. Org. Chem.
2004,
3633
5a Geysen HM.
Meloen RH.
Barteling SJ.
Proc. Natl. Acad. Sci. U.S.A.
1984,
81:
3998
5b Subra G.
Soulère L.
Hoffmann P.
Enjalbal C.
Aubagnac J.-L.
Martinez J.
QSAR Comb. Sci.
2003,
22:
646
5c Feliu L.
Subra G.
Martinez J.
Amblard M.
J. Comb. Chem.
2003,
5:
356
6a Loupy A.
Microwaves in Organic Synthesis
Wiley-VCH;
Weinheim:
2002.
6b Santagada V.
Perissutti E.
Caliendo G.
Curr. Med. Chem.
2002,
9:
1251
6c Kappe CO.
Angew. Chem. Int. Ed.
2004,
43:
6250
7 Grieco P.
Campiglia P.
Gomez-Monterrey I.
Lama T.
Novellino E.
Synlett
2003,
2216
8 Kates SA.
Solé NA.
Johnson CR.
Hudson D.
Barany G.
Albericio F.
Tetrahedron Lett.
1993,
34:
1549
9 SynPhaseTM lanterns were purchased from Mimotopes, Pty Ltd, Clayton, Australia.
10 After allyl removal, lanterns were washed with CHCl3 -AcOH-NMM (37:2:1, 3 × 2 min), DIPEA-CH2 Cl2 (1:19, 3 × 5 min), sodium N ,N -diethyldithiocarbamate (0.03 M in NMP, 3 × 15 min), NMP (5 × 5 min) and CH2 Cl2 (5 × 5 min).
11 Basso A.
Ernst B.
Tetrahedron Lett.
2001,
42:
6687
12 All microwave experiments were performed using the microwave Ethos SEL labstation from Milestone equipped with a dual magnetron system (1600 W). The experiment time, temperature and power were controlled with the EasyControl software package. The temperature was monitored through the ATC-400FO Automatic Fiber Optic Temperature Control System immersed into a standard Milestone reference vessel. This equipment regulates the power to achieve and maintain the selected temperature. Firstly, a microwave ramp (500 W max.) was applied for 2 Cl2 (3 × 5 min). The compound was cleaved from the lantern using a solution of TFA-H2 O-TIS (95:2.5:2.5). After 1 h at r.t., the lantern was removed, the solution was concentrated under a stream of N2 and the compound was precipitated with dry Et2 O, centri-fuged and decanted. The final cyclopeptide was analyzed by HPLC and characterized by FAB-MS or ESI-MS.
