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Chapter 60,263

Solid-Phase Synthesis of Oxetane Modified Peptides

Beadle, J.D.; Knuhtsen, A.; Hoose, A.; Raubo, P.; Jamieson, A.G.; Shipman, M.

Organic Letters 19(12): 3303-3306

2017

ISSN/ISBN: 1523-7052
PMID: 28585839
DOI: 10.1021/acs.orglett.7b01466
Accession: 060262869
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Solid-phase peptide synthesis (SPPS) is used to create peptidomimetics in which one of the backbone amide C═O bonds is replaced by a four-membered oxetane ring. The oxetane containing dipeptide building blocks are made in three steps in solution, then integrated into peptide chains by conventional Fmoc SPPS. This methodology is used to make a range of peptides in high purity including backbone modified derivatives of the nonapeptide bradykinin and Met- and Leu-enkephalin.

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Related References

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