- Effective synthesis of cyclic peptide yunnanin C and analogues via Ser/Thr ligation (STL)-mediated peptide cyclization
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Cyclic peptide yunnanin C isolated from the root of Stellaria yunnanensis was efficiently synthesized in which the linear peptide was prepared by Boc-SPPS and the cyclization was realized by serine/threonine ligation (STL)-mediated cyclization. In addition, nine yunnanin C analogues, including mutations of Tyr7Gly, Tyr7Val, Tyr7Pro, Tyr7Phe, Ser1Thr, Pro2Val, Gly5Pro, Phe6Ala and Ile4Ala, were prepared in the same fashion. Here, we demonstrated that STL-mediated peptide cyclization could be an effective approach to construct cyclic peptides. Except that proline at the C-terminus could retard the cyclization process, cyclization of yunnanin C analogues with various C-terminal amino acids proceeded with fast cyclization rate (a working concentration of 5 mM.
- Wong, Clarence T.T.,Lam, Hiu Yung,Li, Xuechen
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- Synthesis of constrained head-to-tail cyclic tetrapeptides by an imine-induced ring-closing/contraction strategy
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Making heads or tails of it: A strategy involving a head-to-tail imine-captured ring closure followed by ring contraction was used to synthesize otherwise difficult cyclic tetrapeptides. Compared with the direct lactamization process, the estimated activa
- Wong, Clarence T. T.,Lam, Hiu Yung,Song, Tao,Chen, Guanhua,Li, Xuechen
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- Effective synthesis of kynurenine-containing peptides via on-resin ozonolysis of tryptophan residues: Synthesis of cyclomontanin B
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The preparation of Kyn-containing peptides is difficult, owing to the low reactivity of Kyn in the coupling reaction. In this report, Kyn-containing peptides were efficiently obtained via on-resin ozonolysis of the corresponding Trp-containing peptide. In
- Wong, Clarence T. T.,Lam, Hiu Yung,Li, Xuechen
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supporting information
p. 7616 - 7620
(2013/11/06)
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