Photochemical synthesis of cyclic peptide models from phthalimido acetamides and phthaloyl dipeptide esters
Krüger, Katrin, Lüdke, Virginia, Pettinger, Jonathan, Ashton, Luke, Bonnet, Laetitia, Motti, Cherie, Lex, Johann, and Oelgemöller, Michael (2018) Photochemical synthesis of cyclic peptide models from phthalimido acetamides and phthaloyl dipeptide esters. Tetrahedron Letters, 59 (14). pp. 1427-1430.
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Abstract
The photochemistry of several phthalimido acetamides and phthaloyl dipeptide esters has been investigated. Their photocyclization ability strongly depended on the substitution pattern of the amide linker group. While secondary amide-derived starting materials were largely unreactive, the corresponding tertiary amide-linked derivatives furnished the desired cyclic peptide model compounds in acceptable to good yields (41–80%). The structurally related ester-linked model derivatives also remained unreactive upon irradiation. Preferential hydrogen-abstraction from the E-cis-substituent is suggested to explain the observed differences in cyclization ability.
| Item ID: | 52947 |
|---|---|
| Item Type: | Article (Research - C1) |
| ISSN: | 1873-3581 |
| Keywords: | phthalimide; photochemistry; photocyclization; hydrogen-abstraction; cyclic peptide models |
| Funders: | James Cook University (JCU), Australian Research Council (ARC) |
| Projects and Grants: | JCU CRIG 2011, ARC DP130100794 |
| Date Deposited: | 10 Apr 2018 01:51 |
| FoR Codes: | 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340503 Organic chemical synthesis @ 70% 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340505 Physical organic chemistry @ 30% |
| SEO Codes: | 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100% |
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