Synthese Des Insulins Anfänge und Fortschritte

Using an extraction procedure which permits determination of end‐points, the reduction of a number of tosylamino acids, their derivatives, and model compounds with sodium in liquid ammonia has been investigated. When the molecule contains a single acidic group in addition to the tosylamino group (as in the case of the simple mono‐tosylamino monocarboxylic acids) reduction proceeds with the consumption of 2 g‐at. Na per tosyl group and the formation of toluene‐4‐sulphinic acid. If the number of acidic groups in the products is insufficient to accommodate the number of electrons consumed in the reduction, the reduction of ionisable tosylamino groups is incomplete unless an acid is added. If the number of acidic groups is higher, or excess acid is added, the sulphur‐containing products include thiocresol and sulphite. This last reaction course is also observed whenever calcium is used in place of sodium. A partial interpretation of the results is offered.

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Totalsynthese von Humaninsulin unter gezielter Bildung der Disulfidbindungen. Vorläufige Mitteilung

Sieber

Kamber

Hartmann

et al. 1974

Helvetica Chimica Acta

131

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A preliminary account is given of a total synthesis of human insulin involving directed formation of the three disulfide bonds a t different stages of the fragment-condensation approach. The synthesis was facilitated by the application of two new methods for the selective removal of protecting groups. I n the first, two S-Trt-protected cysteine residues are converted to the disulfide without affecting S-Acm-protected cysteine residues. The second new method consists in a very mild, pH-controllcd, acidolysis of N(a)-Trt, leaving intact N(a)-Bpoc and other acid-labile protecting groups. The last step of the synthesis was the formation of the disulfide bridge between the Acm-protected cysteine residues A7 and B7 by iodine. Extensive countercurrent distribution yielded the synthetic hormone in pure form. It was compared and found to be identical with natural human insulin. Identification was achieved by means of thinlayer chromatography and electrophoretic procedures, as well as by comparing the pattern of breakdown by enzymes (finger-printing). The natural and synthetic hormones were crystallized under identical conditions. The synthetic human insulin was found to possess full biological activity in an in vitvo system.

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Synthese Des Insulins Anfänge und Fortschritte

Cited by 11 publications

References 159 publications

Chemische Synthese von Peptidhormonen

Chemische Synthese von Peptidhormonen

Reduction of Tosylamino Acids and Related Compounds with Sodium in Liquid Ammonia; stoichiometry and products

Totalsynthese von Humaninsulin unter gezielter Bildung der Disulfidbindungen. Vorläufige Mitteilung

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