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Hormone-Receptor Interactions. Synthesis and Conformational Study of cyclo-L-Cystathionine

✍ Scribed by Jean-Luc Fauchère; Natesa Muthukumaraswamy; Aung Tun-Kyi; Robert Schwyzer

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
493 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The purpose of this work was to see whether the replacement of a sulfur atom in a cystine disulfide bridge by a methylene group is an only superficial ‘isosteric’ substitution, i.e. with regard to size, hydrophobia, bond angles, etc., or whether it would also encompass such parameters as preferred conformations in solution (M‐ or P‐helicity of the bridge). The methods involved the synthesis of a model compound, cyclo‐L‐cystathionine (cyclo‐L‐carbacystine), and its investigation by ^1^H‐ and ^13^C‐NMR. It is concluded that the conformations of the CH~2~(β)CH~2~(γ)SCH~2~(β') bridge, and of the diketopiperazine ring are closely similar to the analogous elements in cyclo‐L‐cystine (DMSO as solvent). This knowledge might help to explain the fact that carba analogs of heterodetic‐cyclic polypeptide hormones are often biologically very active.

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