Synthesis and cytotoxicity of a new class of potent decapeptide macrocycles

Organic Letters

Volumn 10, Issue 2, 2008, Pages 177-180

  Davis, Melinda R ^a   Styers, Thomas J ^a   Rodriguez, Rodrigo A ^a   Pan, Po Shen ^a   Vasko, Robert C ^a   McAlpine, Shelli R ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DEPSIPEPTIDE; SANSALVAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; DRUG EFFECT; DRUG RESISTANCE; DRUG SCREENING; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; DEPSIPEPTIDES; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 38749144034     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702403r     Document Type: Article

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30. 1H NMR were taken for cyclized peptides, but due to their complexity, they were not seen as the primary confirmation for cyclized compounds). See the Supporting Information for spectra.
31. Unpublished results from the Guy laboratory at the Department of Chemical Biology and Therapeutics, St Jude Children's Research Hospital, Memphis, TN 38103, and published results from our laboratory show that the use of several coupling reagents facilitates formation of the peptide bond in high yields.
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33. For details on the reaction conditions, see the Supporting Information.
34. It was straightforward to follow the reactions via LCMS as the starting material double-deprotected linear precursor would appear at 5.0-5.5 min and the cyclized product would appear between 6.1 and 7.0 min.