Journal article
Iterative Reducible Ligation to form Homogeneous Penicillamine Cross-linked Polypeptides
Tetrahedron letters, Vol.54(26), pp.3440-3443
06/26/2013
DOI: 10.1016/j.tetlet.2013.04.086
PMCID: PMC3857801
PMID: 24347694
Abstract
The syntheses of homogeneous penicillamine disulfide cross-linked polypeptides are reported. Dodecapeptides containing N-terminal, C-terminal, or N- and C-terminal Pen were serially ligated into 36 amino acid polypeptides linked through Cys-Pen, Pen-Cys or Pen-Pen disulfide bonds. Critical to the syntheses was the incorporation of thiazolidine masked Cys and Pen as the N-terminal residues and selective hydrolysis with silver trifluoromethanesulfonate in acidic aqueous conditions to generate a free thiol for subsequent ligation. This approach allows the synthesis of homogeneous disulfide cross-linked polypeptides that have different reductive stabilities and have application in gene delivery by undergoing a tempered reductive triggered release of DNA.
Details
- Title: Subtitle
- Iterative Reducible Ligation to form Homogeneous Penicillamine Cross-linked Polypeptides
- Creators
- Mark D Ericson - Division of Medicinal & Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City IA 52242Kevin G Rice - Division of Medicinal & Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City IA 52242
- Resource Type
- Journal article
- Publication Details
- Tetrahedron letters, Vol.54(26), pp.3440-3443
- DOI
- 10.1016/j.tetlet.2013.04.086
- PMID
- 24347694
- PMCID
- PMC3857801
- NLM abbreviation
- Tetrahedron Lett
- ISSN
- 0040-4039
- eISSN
- 1873-3581
- Publisher
- England
- Grant note
- T32 GM008365 / NIGMS NIH HHS R01 GM087653 / NIGMS NIH HHS
- Language
- English
- Date published
- 06/26/2013
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Craniofacial Anomalies Research Center; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984065315102771
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