caa a22 4500 477136877 CHVBK 20180405111721.0 cr unu---uuuuu 170330e19970101xx s 000 0 eng 10.1007/BF00127963 doi (NATIONALLICENCE)springer-10.1007/BF00127963 Evaluation of strategies for ‘one-pot' deprotection, cleavage and disulfide bond formation in the preparation of cystine-containing peptides [Elektronische Daten] [Jane Spetzler, Morten Meldal] Summary: Oxytocin, a nonapeptide amide, was synthesized on a PEGA-resin using the Fmoc-tBu strategy. The sulfhydryl groups of the two cysteine residues were protected with trityl groups. Different oxidation reagents such as DMSO, I2 and thallium (III) trifluoroacetate mixed with TFA were evaluated in order to obtain oxytocin in a one-pot reaction. The mixture of TFA and DMSO (5:1) in which oxytocin was formed quantitatively was found to be the optimal method. The cyclic oxytocin could be isolated in 56% yield. ESCOM Science Publishers B.V., 1997 Disulfide bond nationallicence DMSO oxidation nationallicence Oxytocin nationallicence Peptide synthesis nationallicence TFA cleavage nationallicence Acm : acetamidomethyl nationallicence DCM : dichloromethane nationallicence Dhbt : 3,4-dihydro-4-oxobenzotriazin-3-yl nationallicence DMF : dimethylformamide nationallicence DMSO : dimethylsulfoxide nationallicence Fmoc : 9-fluorenylmethyloxycarbonyl nationallicence MALDI : matrix-assisted laser desorption ionisation nationallicence NEM : 4-ethylmorpholine nationallicence PEGA : polyethylene glycol-poly-N,N-dimethylacrylamide co-polymer nationallicence Pfp : pentafluorophenyl nationallicence TBTU : O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate nationallicence t Bu : tert-butyl nationallicence TFA : trifluoroacetic acid nationallicence TIS : triisopropylsilane nationallicence Tl(tfa)3 : thallium(III) trifluoroacetate nationallicence Trt, triphenylmethyl nationallicence Spetzler Jane Department of Chemistry, Carlsberg Laboratory, Gamle Carlsberg Vej 10, DK-2500, Valby, Denmark aut Meldal Morten Department of Chemistry, Carlsberg Laboratory, Gamle Carlsberg Vej 10, DK-2500, Valby, Denmark aut Letters in Peptide Science Kluwer Academic Publishers 3/6(1997-01-01), 327-332 0929-5666 3:6<327 1997 3 10989 https://doi.org/10.1007/BF00127963 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00127963 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Spetzler Jane Department of Chemistry, Carlsberg Laboratory, Gamle Carlsberg Vej 10, DK-2500, Valby, Denmark aut NATIONALLICENCE 700 1- Meldal Morten Department of Chemistry, Carlsberg Laboratory, Gamle Carlsberg Vej 10, DK-2500, Valby, Denmark aut NATIONALLICENCE 773 0- Letters in Peptide Science Kluwer Academic Publishers 3/6(1997-01-01), 327-332 0929-5666 3:6<327 1997 3 10989 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer