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. 2008;47(36):6851-5.
doi: 10.1002/anie.200705471.

An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation

Juan B Blanco-Canosa  1 , Philip E Dawson
Affiliations

An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation

Juan B Blanco-Canosa et al. Angew Chem Int Ed Engl. 2008.
No abstract available

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Figures

Figure 1
Figure 1
Synthesis, thioester exchange and ligation of LYRAG-Nbz. A) HPLC chromatogram of crude LYRAG-Nbz. B) Thiolysis of crude LYRAG-Nbz in 200 mM MPAA, pH 7.0 after 1 h. C) Ligation of CRAFS to LYRAG-Nbz after 50 min, pH 7.0
Figure 2
Figure 2
Rvg-Nbz HPLC and ESI mass of crude synthetic product. Mass observed: [M+H] 3426.0 Da, (calculated: [M+H] 3426.8 Da). Rvg sequence: YTIWMPENPRPGTPCDIFTNSRGKRASNG-Nbz.
Figure 3
Figure 3
Ligation of Rvg-Nbz and Tsr (N-terminal Cys, 30 aa). HPLC traces are shown at 0 and 2 h. RvgTsr, mass observed: [M+H] 6367.0 Da, (calculated: 6367.3 Da).
Scheme 1
Scheme 1
Synthetic strategy for Fmoc-SPPS of thioester peptides. Following SPPS, aminoanilide 1 undergoes specific acylation and cyclization to yield the resin bound acylurea peptide 2. Following cleavage and deprotection, peptide-Nbz 3 can undergo thiolysis to yield peptide thioester 4, or direct ligation to yield the native peptide 5.
Scheme 2
Scheme 2
Synthesis of LYRAG-Nbz. TIS=triisopropylsilane, Pbf=2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl.
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References

    1. Aimoto S. Biopolymers. 1999;51:247–265. - PubMed
    1. Camarero JA, Adeva A, Muir TW. Lett Pept Sci. 2000;7:17–21.
    1. Dawson PE, Kent SB. Annu Rev Biochem. 2000;69:923–960. - PubMed
    1. Schnolzer M, Alewood P, Jones A, Alewood D, Kent SBH. Int J Pept Res Ther. 2007;13:31–44.
    1. Hackeng TM, Griffin JH, Dawson PE. Proc Natl Acad Sci USA. 1999;18:10068–10073. - PMC - PubMed

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