Synthesis of cyclic peptides via efficient new coupling reagents

Ehrlich, Angelika; Rothemund, Sven; Brudel, M.; Beyermann, Michael; Carpino, Louis A.; Bienert, Michael

doi:10.1016/s0040-4039(00)74087-1

Cited by 74 publications

(30 citation statements)

References 13 publications

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“…41 Much work has been carried out with variation of the substituents, yielding HAPyU 31 (also named BBC by Chen 42 ) and TAPipU 32 with relatively little impact on the outcome of couplings. 43 Other modifications include HAPipU 37 33a, HBPipU 44 33b, HAMDU 37 34a, HBMDU 37 34b (also named BOI), and HAMTU 37 35. Overall the structural differences between these reagents did not appear to be based on rational considerations and were merely a screening of different substituents.…”

Section: Uronium/aminium Saltsmentioning

confidence: 99%

Amide bond formation: beyond the myth of coupling reagents

2009

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Amide bond formation is a fundamentally important reaction in organic synthesis, and is typically mediated by one of a myriad of so-called coupling reagents. This critical review is focussed on the most recently developed coupling reagents with particular attention paid to the pros and cons of the plethora of "acronym" based reagents. It aims to demystify the process allowing the chemist to make a sensible and educated choice when carrying out an amide coupling reaction (179 references).

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Section: Uronium/aminium Saltsmentioning

confidence: 99%

Amide bond formation: beyond the myth of coupling reagents

2009

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“…PyBroP, HOAt, HOBt, SbCl 5 , DCC, KPF 6 , 2‐fluoro pyridine were purchased from Aldrich Chemical Co. (Milwaukee, WI, USA) and used without purification. Pyrrolidine, pentafluorophenol and 2‐bromopyridine were from Acros Corp. Fmoc‐Nva‐OH, Fmoc‐Sar‐OH were from Peptide International Inc. HBTU, BOP and PyBOP were from Calbiochem‐Novabiochem Corp. PyClU, BTFFH, HBPyU, HAPyU and HBPipU were prepared as described previously (6,7,12,23).…”

Section: Methodsmentioning

confidence: 99%

“…In recent decades, many coupling reagents have been designed, synthesized and commonly used in peptide synthesis, and even in the field of organic synthesis (1,2). Among these reagents, HOBt‐ and HOAt‐based uronium and phosphonium salts, such as BOP (3), PyBOP (4), HBTU (5), HBPyU (6,7), HBMDU (8), AOP (9), PyAOP (10), HATU (11), HAPyU (12) and HAMDU (13), have proved to be very efficient (Fig. 1).…”

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confidence: 99%

The development of highly efficient onium‐type peptide coupling reagents based upon rational molecular design

2001

The Journal of Peptide Research

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Novel and highly efficient immonium-, pyridinium- and thiazolium-type peptide coupling reagents, such as BOMI, BDMP, BPMP, BEP, FEP, BEPH, FEPH and BEMT, were developed by rational modifying of the molecular structures of commonly used uronium-type reagents. The high efficiency of these onium salts has been evaluated and proven by model reaction tests and the successful synthesis of various oligopeptides and biologically active peptides, both in solution and in the solid-phase, for example Leu-enkephalin, the pentapeptide moiety of Dolastatin 15 and the immunosuppressive undecapeptide cyclosporin O. Based upon these results, the relationship between the molecular structure and the capability of onium-type peptide coupling reagents was studied. A preliminary guideline for the molecular design of onium-type coupling reagents was developed.

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“…The disubstituted benzotriazole derivative CF 3 -NO 2 -PyBOP (59) [4-nitro-6-(trifluoromethyl) benzotriazol-1-yl)oxy]tris-(pyrrolidino)phosphonium hexafluorophosphate [50a, 57] has been prepared by reaction of PyBrOP (49) with the corresponding disubstituted hydroxybenzotriazole. The dimethylamine and pyrrolidine phosphoramide derivatives AOP (55) and PyAOP (56) have been prepared in the same way [58], as well as the phosphonium salt PyDOP (63) and PyDAOP (64), by reaction of the corresponding additive with the phosphonium salt PyCloP (48) in the presence of TEA [44,59]. Pentafluorophenol and -thiophenol derivatives of tris(pyrrolidino) phosphine oxide 61 (PyPOP) and 62 (PyPSP) [49] have also been obtained by reaction…”

Section: Preparation Of Phosphonium Saltsmentioning

confidence: 99%