81135-27-5Relevant academic research and scientific papers
Total synthesis of cyclosporine: Access to N-methylated peptides via lsonitrile coupling reactions
Wu, Xiangyang,Stockdill, Jennifer L.,Wang, Ping,Danishefsky, Samuel J.
supporting information; experimental part, p. 4098 - 4100 (2010/05/15)
Recent developments in the use of isonitriles to furnish secondary and tertiary amide bond formations have been applied to a novel total synthesis of the important cyclic polypeptide cyclosporine A. Specifically, the disclosed synthetic route demonstrates the utility of microwave-mediated carboxylic acid isonitrile couplings, thioacid isonitrile couplings at ambient temperature, and isonitrile-mediated couplings of carboxylic acids and thioacids with amines to form challenging amide bonds. Copyright
Total synthesis of cyclosporin O by convergent approach employing Fmoc-amino acid chlorides mediated by zinc dust
Tantry, Subramanyam J.,Venkataramanarao, Rao,Chennakrishnareddy, Gundala,Sureshbabu, Vommina Venkata
, p. 9360 - 9363 (2008/03/14)
(Chemical Equation Presented) An epimerization free and efficient total synthesis of immunosuppressant cyclosporin O (CsO) by step-by-step assembly of amino acids in solution phase is reported. The couplings were performed by employing Fmoc-amino acid chl
Total synthesis of cyclosporin O both in solution and in the solid phase using novel thiazolium-, immonium-, and pyridinium-type coupling reagents: BEMT, BDMP, and BEP
Li, Peng,Xu, Jie Cheng
, p. 2951 - 2958 (2007/10/03)
Cyclosporin O (1), an extensively N-methylated immunosuppressive cyclic undecapeptide isolated from Tolypocladium inflatum Gams, was synthesized in 20-23% overall yield via 4 + 7 segment condensation and cyclization by the combined utilization of novel thiazolium- and immonium-type peptide coupling reagents 2-bromo-3-ethyl-4-methyl thiazolium tetrafluoroborate (BEMT) and 5- (1H-benzotriazol-1-yloxy)-3,4-dihydro-1-methyl 2H-pyrrolium hexachloroantimonate (BDMP) as well as compound 2-bromo-1-ethyl pyridinium tetrafluoroborate (BEP). BEMT and BEP, which have been proven to be very efficient for the coupling of peptide segments containing N-alkylated amino acid residues with respect to the fast reaction speed, low racemization, and high yields, were used to construct hindered amide bonds in CsO with the addition of HOAt, whereas the most efficient HOBt-derived immonium type reagent, BDMP, was used to perform the coupling of coded amino acids in CsO. Thus, the highly hindered protected 8-11 tetrapeptide 25 was successfully synthesized using BEMT in 65% yield, and the 1-7 heptapeptide 21 was obtained in 52-55% yield by the rationally combined utilization of BDMP, BEMT, and BEP. The synthesis of the linear undecapeptide 27 of CsO in the solid phase using BEMT and BEP was accomplished for the further evaluation of the effectiveness of these reagents.
Synthesis of D-lysine8-cyclosporine A. Further characterization of BOP-C1 in the 2-7 hexapeptide fragment synthesis
Colucci,Tung,Petri,Rich
, p. 2895 - 2903 (2007/10/02)
The coupling reagent N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) has been used to synthesize the 2-7 hexapeptide fragment of cyclosporine A. The reagent proved useful in four of the five coupling steps with yields ranging from 78 to 92%. Ove
