Solution versus solid-phase cyclization strategies for large sidechain lactam-bridged peptides: a comparative study.

J A Camarero; J J Cairó; E Giralt; D Andreu

doi:10.1002/psc.310010405

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Solution versus solid-phase cyclization strategies for large sidechain lactam-bridged peptides: a comparative study.

J A Camarero·J J Cairó·E Giralt·D Andreu

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Abstract

A 22-residue peptide with a sidechain lactam bridge involving 18 residues (60-atom cycle) has been synthesized. Three different protection schemes using Fmoc/tBu/cyclohexyl, Fmoc/tBu/allyl or Boc/Bzl/ fluorenylmethyl protecting group combinations have been explored for the solid phase of the linear precursors, which have been subsequently cyclized in solution or in the solid phase. Cyclization yields in solution have been consistently better than on solid phase; however, the solid-phase strategy requires fewer purification steps and therefore global yields are comparable.

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Amino Acid Sequence Chromatography, High Pressure Liquid Indicators and Reagents Lactams Methods Molecular Sequence Data Molecular Structure Peptides, Cyclic Solutions Comparative Study Journal Article Research Support, Non-U.S. Gov't

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J A Camarero, J J Cairó, E Giralt, D Andreu. Solution versus solid-phase cyclization strategies for large sidechain lactam-bridged peptides: a comparative study.. https://doi.org/10.1002/psc.310010405

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