Universität zu Köln

Kruger, Katrin, Ludke, Virginia, Pettinger, Jonathan ORCID: 0000-0002-8219-8369, Ashton, Luke, Bonnet, Laetitia, Motti, Cherie A., Lex, Johann and Oelgemoller, Michael ORCID: 0000-0003-3541-6770 (2018). Photochemical synthesis of cyclic peptide models from phthalimido acetamides and phthaloyl dipeptide esters. Tetrahedron Lett., 59 (14). S. 1427 - 1431. OXFORD: PERGAMON-ELSEVIER SCIENCE LTD. ISSN 0040-4039

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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. (C) 2018 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Kruger, Katrin UNSPECIFIED UNSPECIFIED UNSPECIFIED Ludke, Virginia UNSPECIFIED UNSPECIFIED UNSPECIFIED Pettinger, Jonathan UNSPECIFIED orcid.org/0000-0002-8219-8369 UNSPECIFIED Ashton, Luke UNSPECIFIED UNSPECIFIED UNSPECIFIED Bonnet, Laetitia UNSPECIFIED UNSPECIFIED UNSPECIFIED Motti, Cherie A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Lex, Johann UNSPECIFIED UNSPECIFIED UNSPECIFIED Oelgemoller, Michael UNSPECIFIED orcid.org/0000-0003-3541-6770 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-189682
DOI:	10.1016/j.tetlet.2018.02.074
Journal or Publication Title:	Tetrahedron Lett.
Volume:	59
Number:	14
Page Range:	S. 1427 - 1431
Date:	2018
Publisher:	PERGAMON-ELSEVIER SCIENCE LTD
Place of Publication:	OXFORD
ISSN:	0040-4039
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SUBSTITUTED N-ALKYLPHTHALIMIDES; ALPHA-AMINO-ACIDS; CONFORMATIONAL FLEXIBILITY; AQUEOUS-SOLUTION; PHOTOCYCLIZATION; DERIVATIVES; PROTEINS; DECARBOXYLATION; HYDROPYRAZINES; SPECTROSCOPY Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/18968