109745-89-3Relevant articles and documents
Oxybenzotriazole free peptide coupling reagents for N-methylated amino acids
Coste, Jacques,Frerot, Eric,Jouin, Patrick,Castro, Bertrand
, p. 1967 - 1970 (1991)
The main product of N-methylated amino acid coupling, when oxybenzotriazole is present in the reagent (BOP, PyBOP, HBPyU) or as an additive (DCC/HOBt), is the weakly reactive benzotriazolyl ester. On the other hand, the corresponding new halogenated reage
Coupling N-Methylated Amino Acids Using PyBroP and PyCloP Halogenophosphonium Salts: Mechanism and Fields of Application
Coste, Jacques,Frerot, Eric,Jouin, Patrick
, p. 2437 - 2446 (1994)
PyBroP (1) and PyCloP (2), two halotripyrrolidinophosphonium hexafluorophosphates, are peptidecoupling reagents highly efficient for coupling N-methylated amino esters, in contrast with PyBOP (3), the hydroxybenzotriazolyl analogue.These halogenophosphonium salts 1 and 2 are convenient (one-pot reactions) stable solids soluble in conventional solvents.Use of them gave an excellent peptide yield with essentially no epimerization.Activation with these reagents probably involves the formation of an (acyloxy)phosphonium, as shown in the case of 2,4,6-trimethylbenzoic acid activation.In the case of reagents 1 and 2, oxazolone and/or a symmetrical anhydride were intermediates which were rapidly aminolyzed.In contrast, the benzotriazolyl ester intermediate which was formed with PyBOP (3) was poorly reactive with N-methylated amino esters.PyBroP (1) and PyCloP (2) were less efficient in the coupling of some Boc-amino acids because of N-carboxyanhydride formation; this was particularly the case when Boc-Val-OH or Boc-MeVal-OH was coupled with MeVal-OMe.
Polymer-bound TBTU as a new solid-supported reagent for peptide synthesis
Chinchilla, Rafael,Dodsworth, David J.,Nájera, Carmen,Soriano, José M.
, p. 2463 - 2466 (2007/10/03)
A new polymer-supported TBTU (P-TBTU) has been prepared from polystyrene-bound 1-hydroxybenzotriazole (P-HOBT) and used efficiently as a solid-supported reagent for peptide-coupling reactions, and is even effective with wet solvents. The P-HOBT can be rec
2-Mercaptopyridone 1-oxide-based uronium salts: New peptide coupling reagents
Bailen, Miguel A.,Chinchilla, Rafael,Dodsworth, David J.,Najera, Carmen
, p. 8936 - 8939 (2007/10/03)
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