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


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.

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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2006
Deposited On:22 May 2012 06:50
Last Modified:05 Apr 2016 15:19
Publisher:Wiley-Blackwell
ISSN:0108-2701
Publisher DOI:https://doi.org/10.1107/S0108270106007992
Permanent URL: https://doi.org/10.5167/uzh-54213

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