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Synthesis of Deuteriated Derivatives of Diastereomeric Cyclopentapeptides for Use in Conformational Analysis. The syntheses and properties of eight cyclic pentapeptides containing glycine with two deuterium atoms at C(α) (Gly*) are described: cyclo‐[‐Gly‐L‐Cys(DPM)‐Gly‐Gly*‐L‐Pro‐], cyclo‐[‐Gly*‐L‐Cys(DPM)‐Gly‐Gly*‐L‐Pro‐], cyclo‐[‐Gly‐L‐Cys‐(DPM)‐Gly‐Gly*‐D‐Pro‐], cyclo‐[‐Gly*‐L‐Cys(DPM)‐Gly‐Gly*‐D‐Pro‐], cyclo‐[‐Gly‐L‐Ala‐Gly‐Gly*‐L‐Pro‐], cyclo‐[‐Gly*‐L‐Ala‐Gly‐Gly*‐L‐Pro‐], cyclo‐[‐Gly‐L‐Ala‐Gly‐Gly*‐D‐Pro‐], and cyclo‐[‐Gly*‐L‐Ala‐Gly‐Gly*‐D‐Pro‐] (DPM = diphenylmethyl). These particular compounds were chosen in order to assign by NMR. unambiguously certain conformational features, like hydrogen‐bonding and shielding, to individual peptide bonds.
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Möschler et al. (1976) studied this question.
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