Di- and tripeptide segments of zervamicin II-2: Z-Thr(OBn)-Aib-N(Me)Ph and Z-Val-Aib-Hyp(OBn)-OMe - Zurich Open Repository and Archive

Linden, A; Pradeille, N; Heimgartner, H (2006). Di- and tripeptide segments of zervamicin II-2: Z-Thr(OBn)-Aib-N(Me)Ph and Z-Val-Aib-Hyp(OBn)-OMe. Acta Crystallographica. Section C, Crystal Structure Communications, 62(5):o249-o252.

Abstract

The title compounds, O-benzyl-N-(benzyl­oxy­carbonyl)­threonyl-2,N-dimethyl­alanin­anilide, C30H35N3O5, and methyl (4R)-4-benzyl­oxy-N-(benzyl­oxy­carbonyl)­valyl-2-(methyl­alanyl)prolinate, C30H39N3O7, were obtained from the azirine coupling' of the corresponding protected amino acids with 2,2,N-trimethyl-2H-azirin-3-amine and methyl (4R)-4-(benzyl­oxy)-N-(2,2-dimethyl-2H-azirin-2-yl)prolinate, respectively. The Aib unit in each mol­ecule has the greatest turn- or helix-inducing effect on the mol­ecular conformation. Inter­molecular N—H⋯O inter­actions link the mol­ecules of the tripeptide into sheets and those of the dipeptide into extended chains.

Abstract

The title compounds, O-benzyl-N-(benzyl­oxy­carbonyl)­threonyl-2,N-dimethyl­alanin­anilide, C30H35N3O5, and methyl (4R)-4-benzyl­oxy-N-(benzyl­oxy­carbonyl)­valyl-2-(methyl­alanyl)prolinate, C30H39N3O7, were obtained from the azirine coupling' of the corresponding protected amino acids with 2,2,N-trimethyl-2H-azirin-3-amine and methyl (4R)-4-(benzyl­oxy)-N-(2,2-dimethyl-2H-azirin-2-yl)prolinate, respectively. The Aib unit in each mol­ecule has the greatest turn- or helix-inducing effect on the mol­ecular conformation. Inter­molecular N—H⋯O inter­actions link the mol­ecules of the tripeptide into sheets and those of the dipeptide into extended chains.

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Item Type: Journal Article, refereed, original work 07 Faculty of Science > Department of Chemistry 540 Chemistry English 2006 22 May 2012 06:50 05 Apr 2016 15:19 Wiley-Blackwell 0108-2701 https://doi.org/10.1107/S0108270106007992

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