| N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis. | |
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MedLine Citation:
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PMID: 16316237 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A new generation of triazine-based coupling reagents (TBCRs), designed according to the concept of "superactive esters", was obtained by treatment of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium (DMTMM) chloride with lithium or silver tetrafluoroborate. The structure of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborate was confirmed by X-ray diffraction. Activation of carboxylic acids by using this reagent proceeds via triazine "superactive ester". The coupling reagent was successfully used for the synthesis of Z-, Boc-, and Fmoc-protected dipeptides derived from natural and unnatural sterically hindered amino acids and for fragment condensation, in 80-100% yield and with high enantiomeric purity. The manual SPPS of the ACP(65-74) peptide fragment (H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-OH) proceeded significantly faster than with TBTU or HATU, as well as the automated SPPS of the same fragment gave a purer product than by using TBTU or PyBOP. The reagent was also demonstrated to be efficient in on-resin head-to-tail cyclization of constrained cyclopeptides, in SPPS synthesis of Aib peptides, and in the synthesis of esters from appropriate acids, alcohols, and phenols. The high efficiency and versatility of this new generation of TBCRs confirm, for the first time, the usefulness of the concept of "superactive esters" in rational design of the structure of coupling reagents. |
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Authors:
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Zbigniew J Kami?ski; Beata Kolesi?ska; Justyna Kolesi?ska; Giuseppina Sabatino; Mario Chelli; Paolo Rovero; Micha? B?aszczyk; Marek L G??wka; Anna Maria Papini |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 127 ISSN: 0002-7863 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2005 Dec |
Date Detail:
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Created Date: 2005-11-30 Completed Date: 2006-02-16 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 16912-20 Citation Subset: IM |
Affiliation:
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Institute of Organic Chemistry, ??d? University of Technology, Poland. kaminsz@mail.p.lodz.pl |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amides
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chemical synthesis Amino Acids / chemistry Borates / chemical synthesis, chemistry* Esters / chemical synthesis Fluorenes / chemistry Molecular Structure Morpholines / chemical synthesis, chemistry Oligopeptides / chemical synthesis Peptides / chemical synthesis* Peptides, Cyclic / chemical synthesis Silver Compounds / chemistry Triazines / chemical synthesis, chemistry* X-Ray Diffraction |
| Chemical | |
Reg. No./Substance:
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0/4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; 0/Amides; 0/Amino Acids; 0/Borates; 0/Esters; 0/Fluorenes; 0/Morpholines; 0/N(alpha)-fluorenylmethyloxycarbonylamino acids; 0/Oligopeptides; 0/Peptides; 0/Peptides, Cyclic; 0/Silver Compounds; 0/Triazines; 14104-20-2/silver tetrafluoroborate |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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