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Crystal structure of N-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (Boc–Phe–ΔAla–OiPr)

In the title compound, the de­hydro­dipeptide (Boc–Phe–ΔAla–OiPr, C(20)H(28)N(2)O(5)), the mol­ecule has a trans conformation of the N-methyl­amide group. The geometry of the de­hydro­alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation betwe...

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Autores principales: Lenartowicz, Paweł, Makowski, Maciej, Zarychta, Bartosz, Ejsmont, Krzysztof
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257372/
https://www.ncbi.nlm.nih.gov/pubmed/25553003
http://dx.doi.org/10.1107/S1600536814025197
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author Lenartowicz, Paweł
Makowski, Maciej
Zarychta, Bartosz
Ejsmont, Krzysztof
author_facet Lenartowicz, Paweł
Makowski, Maciej
Zarychta, Bartosz
Ejsmont, Krzysztof
author_sort Lenartowicz, Paweł
collection PubMed
description In the title compound, the de­hydro­dipeptide (Boc–Phe–ΔAla–OiPr, C(20)H(28)N(2)O(5)), the mol­ecule has a trans conformation of the N-methyl­amide group. The geometry of the de­hydro­alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the H(2)C=C group and the peptide bond. The bond angles around de­hydro­alanine have unusually high values due to the steric hindrance, the same inter­action influencing the slight distortion from planarity of the de­hydro­alanine. The mol­ecule is stabilized by intra­molecular inter­actions between the isopropyl group and the N atoms of the peptide main chain. In the crystal, an N—H⋯O hydrogen bond links the mol­ecules into ribbons, giving a herringbone head-to-head packing arrangement extending along the [100] direction. In the stacks, the mol­ecules are linked by weak C—H⋯O hydrogen-bonding associations.
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spelling pubmed-42573722014-12-31 Crystal structure of N-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (Boc–Phe–ΔAla–OiPr) Lenartowicz, Paweł Makowski, Maciej Zarychta, Bartosz Ejsmont, Krzysztof Acta Crystallogr Sect E Struct Rep Online Research Communications In the title compound, the de­hydro­dipeptide (Boc–Phe–ΔAla–OiPr, C(20)H(28)N(2)O(5)), the mol­ecule has a trans conformation of the N-methyl­amide group. The geometry of the de­hydro­alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the H(2)C=C group and the peptide bond. The bond angles around de­hydro­alanine have unusually high values due to the steric hindrance, the same inter­action influencing the slight distortion from planarity of the de­hydro­alanine. The mol­ecule is stabilized by intra­molecular inter­actions between the isopropyl group and the N atoms of the peptide main chain. In the crystal, an N—H⋯O hydrogen bond links the mol­ecules into ribbons, giving a herringbone head-to-head packing arrangement extending along the [100] direction. In the stacks, the mol­ecules are linked by weak C—H⋯O hydrogen-bonding associations. International Union of Crystallography 2014-11-29 /pmc/articles/PMC4257372/ /pubmed/25553003 http://dx.doi.org/10.1107/S1600536814025197 Text en © Lenartowicz et al. 2014 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Lenartowicz, Paweł
Makowski, Maciej
Zarychta, Bartosz
Ejsmont, Krzysztof
Crystal structure of N-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (Boc–Phe–ΔAla–OiPr)
title Crystal structure of N-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (Boc–Phe–ΔAla–OiPr)
title_full Crystal structure of N-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (Boc–Phe–ΔAla–OiPr)
title_fullStr Crystal structure of N-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (Boc–Phe–ΔAla–OiPr)
title_full_unstemmed Crystal structure of N-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (Boc–Phe–ΔAla–OiPr)
title_short Crystal structure of N-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (Boc–Phe–ΔAla–OiPr)
title_sort crystal structure of n-(tert-but­oxy­carbon­yl)phenyl­alanylde­hydro­alanine isopropyl ester (boc–phe–δala–oipr)
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257372/
https://www.ncbi.nlm.nih.gov/pubmed/25553003
http://dx.doi.org/10.1107/S1600536814025197
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