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Synthese von Peptid‐Zwischenprodukten für den Aufbau eines corticotrop wirksamen Nonadecapeptids. I. N ϵ ‐t‐Butyloxycarbonyl‐ L ‐lysin, N ϵ ‐(N ϵ ‐t‐Butyloxycarbonyl‐ L ‐lysyl)‐N ϵ ‐t‐butyloxycarbonyl‐ L ‐lysin, N ϵ ‐t‐Butyloxycarbonyl‐ L ‐lysyl‐ L ‐prolyl‐ L ‐valyl‐glycin und Derivate
Author(s) -
Schwyzer R.,
Rittel W.
Publication year - 1961
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19610440121
Subject(s) - chemistry , trifluoroacetic acid , lysine , amide , hydrolysis , stereochemistry , aqueous solution , acetic acid , peptide , peptide synthesis , amino acid , organic chemistry , biochemistry
For the synthesis of β 1–19 corticotropin‐Glu 5 ‐γ‐amide 1 ) a derivative of lysine was needed involving a blocking group on N ϵ easily removable by mild acid treatment. N ϵ ‐t‐Butoxycarbonyl‐ L ‐lysine was synthesized and found to be a very versatile compound. The N ϵ ‐t‐butoxycarbonyl group is readily removed by trifluoroacetic acid and by aqueous HCI, it is not cleaved by anhydrous or aqueous acetic acid in the experimental conditions described here. This allows its use in conjunction with the N‐trityl group which is easily hydrolysed by aqueous acetic acid. Needless to point out, it may also be used along with the carbobenzoxy or p‐phenylazocarbobenzoxy groups which may preferentially be removed by catalytic hydrogenation. A number of derivatives and peptides of N ϵ ‐t‐butoxycarbonyl‐ L ‐lysine are described, among these are trityl·Lys(BOC)‐Lys(BOC)·OH 7 ) and PZ·Lys(BOC)‐Pro‐Val‐Gly·OH, both intermediates in the synthesis of the nonadecapeptide with high corticotropic activity 1 ). The derivatives described here should also be useful for the preparation of ϵ‐peptides of lysine.