Document Detail

N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis.
MedLine Citation:
PMID:  16316237     Owner:  NLM     Status:  MEDLINE    
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.
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:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  127     ISSN:  0002-7863     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2005 Dec 
Date Detail:
Created Date:  2005-11-30     Completed Date:  2006-02-16     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  16912-20     Citation Subset:  IM    
Institute of Organic Chemistry, ??d? University of Technology, Poland.
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MeSH Terms
Amides / 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
Reg. No./Substance:
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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