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  Solid-phase synthesis of H- and methylphosphonopeptides

Hoffmann, R., Tholey, A., Hoffmann, T., & Kalbitzer, H. R. (1996). Solid-phase synthesis of H- and methylphosphonopeptides. International Journal of Peptide & Protein Research, 47(4), 245-253.

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Genre: Journal Article
Alternative Title : Solid-phase synthesis of H- and methylphosphonopeptides

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IntJPeptProtRes_47_1996_245.pdf (Any fulltext), 776KB
 
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 Creators:
Hoffmann, Ralf, Author
Tholey, A., Author
Hoffmann, T., Author
Kalbitzer, Hans Robert1, Author              
Affiliations:
1Emeritus Group Biophysics, Max Planck Institute for Medical Research, Max Planck Society, ou_1497712              

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Free keywords: electrospray mass spectrometry; peptide phosphorylation; phosphonoserine; phosphonothreonine; phosphor-peptides; 31P NMR spectroscopy
 Abstract: We introduce solid-phase syntheses of H- and methylphosphonopeptides, giving access for the first time to a new class of mimics for o-phosphoamino acids. The model peptides H-GlyGlyXaaAla-OH (Xaa = Ser, Thr) were synthesized on a solid-phase using Fmoc/tBu strategy and HBTU/HOBt activation by incorporation of hydroxyl-protected serine and threonine. As selectively cleavable hydroxyl-protecting groups we used triphenylmethyl and tert-butyldimethylsilyl for both amino acids, as described in the literature. All peptides were phosphitilated with O,O-di-tert-butyl-N,N-diethylphosphoramidite and yielded H-phosphonopeptides after trifluoroacetic acid cleavage. Alternatively we phosphonylated the peptides with O-tert-butyl-N,N-diethyl-P-methylphosphonamidite, which was synthesized by a two-step one-pot procedure starting from commercially available chemicals. All H- and methylphosphonopeptides were obtained in high purities and yields, as shown by reversed-phase high-performance liquid chromatography and anion-exchange chromatography. The phosphonopeptides were characterized by 1H and 31P NMR. We confirmed their molecular masses by electrospray mass spectrometry and analyzed their fragmentation schemes, which seemed to be characteristic for each class of analogues. The H-phosphonopeptides lost phosphonic acid (H3PO3, 82 mass units) and the methylphosphonopeptides lost methylphosphonic acid (MeH2PO3, 96 mass units). Both H- and methylphosphonopeptides represent a new and simply accessible class of mimics for phosphopeptides. Compared with the corresponding phosphopeptides all phosphonopeptides were synthesized in higher yields and purities

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Language(s): eng - English
 Dates: 1995-09-181995-07-061995-10-172009-01-121996-04
 Publication Status: Published in print
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 665224
Other: 6837
 Degree: -

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Title: International Journal of Peptide & Protein Research
  Alternative Title : International Journal of Peptide & Protein Researc
Source Genre: Journal
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Publ. Info: Los Angeles, Calif : Blackwell Munksgaard
Pages: - Volume / Issue: 47 (4) Sequence Number: - Start / End Page: 245 - 253 Identifier: ISSN: 1747-0277