Piv-Proψ[CH2–NH–O]Gly–NHiPr

Corbier, Catherine; Didierjean, Claude; Thévenet, Laurent; Vanderesse, Régis; Marraud, Michel

doi:10.1107/s0108270100006478

Acta Crystallogr C

2000

DOI: 10.1107/s0108270100006478

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Piv-Proψ[CH₂–NH–O]Gly–NHⁱPr

Catherine Corbier¹,

Claude Didierjean²,

Laurent Thévenet

et al.

Abstract: The pseudodipeptide, (S)-N-isopropyl [N-(pivaloyl)pyrrolidin-2-yl]methylaminooxyacetamide, C(15)H(29)N(3)O(3), adopts a global extended conformation with the hydroxylamine group in the g(+)/g(-) structure. The C-terminal amide NH interacts intramolecularly with the hydroxylamine O atom. Both NH bonds of each molecule are hydrogen bonded to the C-terminal amide carbonyl of a neighbouring molecule.

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Cited by 2 publications

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α‐Aminoxy acids as building blocks for the oxime and hydroxylamine pseudopeptide links. Application to the synthesis of human elastase inhibitors

Vanderesse¹,

Thévenet²,

Marraud³

et al. 2003

Journal of Peptide Science

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The aminoxy acids NH2-O-C(alpha)HR-CO2H are much more easily obtained in the enantiomerically pure form than the analogous hydrazino acids NH2-NH-C(alpha)HR-CO2H, and it has been shown that the isosteric amidoxy psi[CO-NH-O] and hydrazide psi[CO-NH-NH] amide surrogates Induce two quite similar gamma-like folded structures. An aminoxy acid can also be N-coupled to a peptide aldehyde to give the aldoxime psi[CH = N-O] link or to a peptide ketone to form the ketoxime psi[CR= N-O] link. The former can be further reduced into the hydroxylamine psi[CH2-NH-O] link which gives rise to reduced amidoxy peptides. The structural properties Induced by these amide surrogates were studied, using IR and NMR spectroscopy, paying particular attention to the Z/E-isomerism of the oxime link. In order to investigate their inhibitory potency, the three amide surrogates were introduced in the Pro3-Val4 and Val4-Ala5 position of Z-Ala1-Ala2-Pro3-Val4-Ala5-Ala6-NHiPr, a substrate which is cleaved in the Val4-Ala5 position by human leukocyte elastase (HLE). The [Val4psi[CO-NH-O]Ala5] analogue was still a substrate, while the [Pro3psi[CO-NH-O]Val4] and [Val4psi[CH = N-O]Ala5] pseudopeptides acted as HLE competitive inhibitors.

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α‐Aminoxy acids as building blocks for the oxime and hydroxylamine pseudopeptide links. Application to the synthesis of human elastase inhibitors

Vanderesse¹,

Thévenet²,

Marraud³

et al. 2003

Journal of Peptide Science

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Syntesis and Crystallographic Structure Studies of N-[5-Methylisoxazole amino-3-yl]-3,5-di-tert-butylsalicylaldimine

et al. 2007

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Amino compounds and their derivatives are very important in molecular biology because of their roles in biochemical reactions. We need more information about their molecular structures in order to learn about their functional roles in biological systems. The formation of amino compound Schiff base intermediates in reactions of biological importance, transmation, racemization and decarboxylation is well documented. In recent years, amino compound Schiff bases have been used as ligands in coordination chemistry. 1,2 Intramolecular electron transfer is a fundamental chemical phenomenon that relates specifically to redox processes that occur in both and systhetic electron-transfer systems. 3 Sterically hindered ligands bearing salicylaldimines are known to be effective antioxidants, and are widely used in the rancidification of fats and oil. 4 Synthesis of crystal. N-[5-Methylisoxazole amino-3-yl]-3,5-ditert-butylsalicylaldimine ligand was synthesised by the reaction of 0.234 g of (3,5-di-tert-butyl-2-hydroxybenzaldehyde) in 25 ml of absolute ethanol and 0.108 g 3-amino-5-methylisoxalc in 20 ml of ethanol. Also 3-4 drops acetic acid were added. The mixture was refluxed for 10 h, followed by cooling to room tempareture. Crystals were filtered, the product was recryztallised from ethanol. The product was soluble in common solvents such as CHCl3, DMF, CH3COCH3 (propanon or aceton) and DMSO. X-ray. Single crystals suitable in size (0.40 × 0.30 × 0.20 mm) x185

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Piv-Proψ[CH₂–NH–O]Gly–NHⁱPr

Cited by 2 publications

References 13 publications

α‐Aminoxy acids as building blocks for the oxime and hydroxylamine pseudopeptide links. Application to the synthesis of human elastase inhibitors

α‐Aminoxy acids as building blocks for the oxime and hydroxylamine pseudopeptide links. Application to the synthesis of human elastase inhibitors

Syntesis and Crystallographic Structure Studies of N-[5-Methylisoxazole amino-3-yl]-3,5-di-tert-butylsalicylaldimine

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