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A new orthogonal protecting group strategy for lanthionine-containing peptides

Groussier, Marianne Françoise Andrée; (2000) A new orthogonal protecting group strategy for lanthionine-containing peptides. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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The synthesis of lanthionine residues bearing photolabile protecting groups and the use of these compounds for the synthesis of lanthionine-containing peptides is described in this thesis. A new orthogonal approach has been developed towards bridged peptidomimetics such as sandostatin analogs. Several synthetic pathways were followed to synthesise these lanthionine residues and several types of photolabile groups were also tried. The final route involves the making of (R, R) lanthionine residues bearing NV and NVOC groups from (^-serine and (R, i?)-cyStine. The intermediates (i^)-cysteine and (7^)-3-iodoalanine were synthesised with the appropriate protecting groups. The iodoalanine intermediates were obtained in high yields as mixtures of rotamers. They were subsequently used to synthesise the final lanthionine residues following a high-yielding and fast route. The formation of small amounts of diastereoisomers was observed. These were easily separated from the final compounds. Photolabile cleavages studies of NV and NVOC groups were carried out and optimised in solution before SPPS. Finally, several attempts at synthesising a sandostatin analog were carried out on a resin, incorporating the lanthionine residues into cyclic octapeptides. Difficulties were encountered during photolabile cleavages on a polystyrene support. However, efficient photolabile cleavage was finally obtained on Tentagel resin. Other sections of this thesis describe the large family of lanthionine-containing peptide lantibiotics and synthetic routes leading to lanthionine residues as well as the different strategies elaborated for the cyclisation of small peptides.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: A new orthogonal protecting group strategy for lanthionine-containing peptides
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
Keywords: Pure sciences; Lanthionine
URI: https://discovery.ucl.ac.uk/id/eprint/10097285
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