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Synthesis of cyclic peptides containing nor-lanthionine bridges via a triply-orthogonal protecting group strategy

Mustapa, MFM; Harris, R; Mould, J; Chubb, NAL; Schultz, D; Driscoll, PC; Tabor, AB; (2002) Synthesis of cyclic peptides containing nor-lanthionine bridges via a triply-orthogonal protecting group strategy. TETRAHEDRON LETT , 43 (46) 8363 - 8366.

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Abstract

We report a new approach to the on-resin synthesis of cyclic peptides containing unnatural thioether side-chain bridges. An orthogonally protected nor-lanthionine was incorporated in a linear precursor peptide via stepwise solid-phase synthesis. This was followed by double allyl deprotection, cyclisation using PyAOP and subsequent chain-cxtension to give an analogue of ring C of nisin. (C) 2002 Elsevier Science Ltd. All rights reserved.

Type:Article
Title:Synthesis of cyclic peptides containing nor-lanthionine bridges via a triply-orthogonal protecting group strategy
Keywords:CONFORMATIONAL PROPERTIES, LANTIBIOTICS, ANALOGS
UCL classification:UCL > School of Life and Medical Sciences > Faculty of Life Sciences > Biosciences (Division of)
UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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