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Titolo:
The development of highly efficient onium-type peptide coupling reagents based upon rational molecular design
Autore:
Li, P; Xu, JC;
Indirizzi:
NCI, Med Chem Lab, NIH, Frederick, MD 21702 USA NCI Frederick MD USA 21702 CI, Med Chem Lab, NIH, Frederick, MD 21702 USA Chinese Acad Sci, Shanghai Inst Organ Chem, Beijing 100864, Peoples R China Chinese Acad Sci Beijing Peoples R China 100864 100864, Peoples R China
Titolo Testata:
JOURNAL OF PEPTIDE RESEARCH
fascicolo: 2, volume: 58, anno: 2001,
pagine: 129 - 139
SICI:
1397-002X(200108)58:2<129:TDOHEO>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
CHLORIDE BOP-CL; METHYLATED AMINO-ACIDS; TETRAMETHYLFLUOROFORMAMIDINIUM HEXAFLUOROPHOSPHATE; PRODUCT; RACEMIZATION; MECHANISM; PYBROP; PYBOP; BOMI;
Keywords:
coupling reagent; molecular design; peptide; racemization; reactivity;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
35
Recensione:
Indirizzi per estratti:
Indirizzo: Li, P NCI, Med Chem Lab, NIH, 376 Boyles St, Frederick, MD 21702 USA NCI 376 Boyles St Frederick MD USA 21702 St, Frederick, MD 21702 USA
Citazione:
P. Li e J.C. Xu, "The development of highly efficient onium-type peptide coupling reagents based upon rational molecular design", J PEPT RES, 58(2), 2001, pp. 129-139

Abstract

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 saltshas been evaluated and proven by model reaction tests and the successful synthesis of various oligopeptides and biologically active peptides, both insolution 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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Documento generato il 24/05/13 alle ore 15:28:49