324753-16-4Relevant articles and documents
Acidic and basic deprotection strategies of borane-protected phosphinothioesters for the traceless Staudinger ligation
Mühlberg, Michaela,Jaradat, Da'san M.M.,Kleineweischede, Rolf,Papp, Ilona,Dechtrirat, Decha,Muth, Silvia,Broncel, Malgorzata,Hackenberger, Christian P.R.
experimental part, p. 3679 - 3686 (2010/08/05)
The traceless Staudinger ligation has recently found various applications in the field of peptide synthesis and modification, including immobilization and cyclization strategies. In this report, we utilize the traceless Staudinger ligation in the formation of amide bonds, which allows the acquisition of acylated aminosugars and peptides as well as the cyclization of peptides. A key element in these synthetic procedures is the use of a borane-protected phosphinomethanethiol, which is demonstrated to be prone towards oxidation in its unprotected form, during the synthesis of phosphinothioesters. In combination with acidic and basic deprotection strategies for the borane-protected phosphinothioesters, amide bonds can be formed in the presence of azides in moderate to good overall yields.
Targeting of polyamidoamine-DNA nanoparticles using the Staudinger ligation: Attachment of an RGD motif either before or after complexation
Parkhouse, Susan M.,Garnett, Martin C.,Chan, Weng C.
, p. 6641 - 6650 (2008/12/21)
Two new methods for the modular synthesis of targeted gene delivery systems are reported. The PEGylated polyamidoamine DMEDA-PEG-DMEDA-(MBA-DMEDA)n+1-PEG-DMEDA 3 was sequentially modified to contain an integrin-binding peptide ligand via the Staudinger ligation. The conjugation of the ligand was achieved either before particle complexation (precomplexation) or after particle complexation (postcomplexation). Comparison of the two systems showed that postcomplexation strategy led to small and discrete toroidal nanoparticles whilst the precomplexation particles showed loose complexes. The targeted particles showed an increased uptake into cells compared to unmodified complexes however no significant increase in transfection was seen.
CHEMICAL SYNTHESIS OF REAGENTS FOR PEPTIDE COUPLING
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Page 21, (2010/02/05)
The present invention provides improved methods for synthesis of phosphinothiol reagents, as well as novel protected reagents, for use in formation of amide bonds, and particularly for peptide ligation. The invention provides phosphineborane complexes useful as reagents in the formation of amide bonds, particularly for the formation of an amide bond between any two of an amino acid, a peptide, or a protein.
