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: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 70%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 30%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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