86061-01-0Relevant articles and documents
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO?) Universal Coupling Reagent for Synthesis in Solution
Fraczyk, Justyna,Kaminski, Zbigniew J.,Katarzynska, Joanna,Kolesinska, Beata
, (2018/01/27)
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO?), a representative member of the inexpensive and environmentally-friendly N-triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO? for peptide synthesis in solution, starting from Z-, Fmoc-, and Boc-protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO? produced high yields, with high crude product purity and low risk of racemization. In all cases, stoichiometric amounts of reagents were used and the standard synthetic procedure, without the need for time-consuming optimization stages or expensive chromatographic purification. DMT/NMM/TsO? was also found to be very useful for the synthesis of oligopeptides using a fragment coupling strategy.
N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis
Kaminski, Zbigniew J.,Kolesinska, Beata,Kolesinska, Justyna,Sabatino, Giuseppina,Chelli, Mario,Rovero, Paolo,Blaszczyk, Michal,Glowka, Marek L.,Papini, Anna Maria
, p. 16912 - 16920 (2007/10/03)
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- lle-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.
Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates
Ziegler, Thomas,Roeseling, Dirk,Subramanian, Lakshminarayanapuram R.
, p. 911 - 914 (2007/10/03)
Several neoglycosyl amino acids possessing a sugar residue, a spacer and a trifunctional amino acid moiety were synthesized both in solution and solid phase by activating the carboxylic group as its pentafluorophenyl ester for condensation. The methodolog