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  A facile Fmoc solid phase synthesis strategy to access pimerization-prone biosynthetic intermediates of glycopeptide antibiotics

Brieke, C., & Cryle, M. (2014). A facile Fmoc solid phase synthesis strategy to access pimerization-prone biosynthetic intermediates of glycopeptide antibiotics. Organic Letters, 16(9), 2454-2457. doi:10.1021/ol500840f.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0019-8F83-1 Version Permalink: http://hdl.handle.net/21.11116/0000-0002-9779-C
Genre: Journal Article

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 Creators:
Brieke, Clara1, Author              
Cryle, Max1, 2, Author              
Affiliations:
1Department of Biomolecular Mechanisms, Max Planck Institute for Medical Research, Max Planck Society, Jahnstrasse 29, 69120 Heidelberg, DE, ou_1497700              
2Cytochrome P450, Max Planck Institute for Medical Research, Max Planck Society, Jahnstrasse 29, 69120 Heidelberg, DE, ou_1497697              

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 Abstract: A rapid protocol based on Fmoc-chemistry for the solid phase peptide synthesis of vancomycin- and teicoplanin-type peptides is described. Epimerization of highly racemization-prone arlyglycine derivatives is suppressed through optimized Fmoc-deprotection and coupling conditions. Starting from easily accessible Fmoc-protected amino acids, this strategy enables the enantioselective synthesis of peptides corresponding to intermediates found in vancomycin and teicoplanin biosynthesis with excellent purity and in high yields (38%–71%).

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Language(s): eng - English
 Dates: 2014-03-202014-04-142014-05-02
 Publication Status: Published in print
 Pages: 4
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ol500840f
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 16 (9) Sequence Number: - Start / End Page: 2454 - 2457 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338