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Crystal structure of N-(tert-but-oxy-carbon-yl)phenyl-alanylde-hydro-alanine isopropyl ester (Boc-Phe-ΔAla-OiPr).

Lenartowicz P, Makowski M, Zarychta B, Ejsmont K - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The geometry of the de-hydro-alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the H2C=C group and the peptide bond.In the crystal, an N-H⋯O hydrogen bond links the mol-ecules into ribbons, giving a herringbone head-to-head packing arrangement extending along the [100] direction.In the stacks, the mol-ecules are linked by weak C-H⋯O hydrogen-bonding associations.

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Affiliation: Faculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland.

ABSTRACT
In the title compound, the de-hydro-dipeptide (Boc-Phe-ΔAla-OiPr, C20H28N2O5), the mol-ecule has a trans conformation of the N-methyl-amide group. The geometry of the de-hydro-alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the H2C=C group and the peptide bond. The bond angles around de-hydro-alanine have unusually high values due to the steric hindrance, the same inter-action influencing the slight distortion from planarity of the de-hydro-alanine. The mol-ecule is stabilized by intra-molecular inter-actions between the isopropyl group and the N atoms of the peptide main chain. In the crystal, an N-H⋯O hydrogen bond links the mol-ecules into ribbons, giving a herringbone head-to-head packing arrangement extending along the [100] direction. In the stacks, the mol-ecules are linked by weak C-H⋯O hydrogen-bonding associations.

No MeSH data available.


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The packing diagram of the title compound, viewed along the b axis, showing the inter­molecular hydrogen-bonding scheme (dashed lines).
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fig2: The packing diagram of the title compound, viewed along the b axis, showing the inter­molecular hydrogen-bonding scheme (dashed lines).

Mentions: In the crystal, strong inter­molecular N8—H⋯O7i hydrogen bonds (Table 1 ▶) link the mol­ecules, giving a herringbone head-to-head packing arrangement, forming ribbons which extend along [100] (Fig. 2 ▶). The ribbon structures are consolidated by weak intra-chain C—H⋯O hydrogen-bonding inter­actions.


Crystal structure of N-(tert-but-oxy-carbon-yl)phenyl-alanylde-hydro-alanine isopropyl ester (Boc-Phe-ΔAla-OiPr).

Lenartowicz P, Makowski M, Zarychta B, Ejsmont K - Acta Crystallogr Sect E Struct Rep Online (2014)

The packing diagram of the title compound, viewed along the b axis, showing the inter­molecular hydrogen-bonding scheme (dashed lines).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257372&req=5

fig2: The packing diagram of the title compound, viewed along the b axis, showing the inter­molecular hydrogen-bonding scheme (dashed lines).
Mentions: In the crystal, strong inter­molecular N8—H⋯O7i hydrogen bonds (Table 1 ▶) link the mol­ecules, giving a herringbone head-to-head packing arrangement, forming ribbons which extend along [100] (Fig. 2 ▶). The ribbon structures are consolidated by weak intra-chain C—H⋯O hydrogen-bonding inter­actions.

Bottom Line: The geometry of the de-hydro-alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the H2C=C group and the peptide bond.In the crystal, an N-H⋯O hydrogen bond links the mol-ecules into ribbons, giving a herringbone head-to-head packing arrangement extending along the [100] direction.In the stacks, the mol-ecules are linked by weak C-H⋯O hydrogen-bonding associations.

View Article: PubMed Central - HTML - PubMed

Affiliation: Faculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland.

ABSTRACT
In the title compound, the de-hydro-dipeptide (Boc-Phe-ΔAla-OiPr, C20H28N2O5), the mol-ecule has a trans conformation of the N-methyl-amide group. The geometry of the de-hydro-alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the H2C=C group and the peptide bond. The bond angles around de-hydro-alanine have unusually high values due to the steric hindrance, the same inter-action influencing the slight distortion from planarity of the de-hydro-alanine. The mol-ecule is stabilized by intra-molecular inter-actions between the isopropyl group and the N atoms of the peptide main chain. In the crystal, an N-H⋯O hydrogen bond links the mol-ecules into ribbons, giving a herringbone head-to-head packing arrangement extending along the [100] direction. In the stacks, the mol-ecules are linked by weak C-H⋯O hydrogen-bonding associations.

No MeSH data available.


Related in: MedlinePlus