Flow-chemistry enabled efficient synthesis of β-peptides: backbone topology vs. helix formation

Imane Nekkaa; Dóra Bogdán; Tamás Gáti; Szabolcs Béni; Tünde Juhász; Márta Palkó; Gábor Paragi; Gábor K. Tóth; Ferenc Fülöp; István M. Mándity

doi:10.1039/C8CC10147G

Flow-chemistry enabled efficient synthesis of β-peptides: backbone topology vs. helix formation†

Imane Nekkaa,‡^a Dóra Bogdán,‡^b Tamás Gáti,^bc Szabolcs Béni,

^d Tünde Juhász,^e Márta Palkó,^a Gábor Paragi,^fg Gábor K. Tóth,^fg Ferenc Fülöp*^a and István M. Mándity

*^abh

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^a Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 7., H-6720 Szeged, Hungary
E-mail: fulop@pharm.u-szeged.hu, mandity.istvan@ttk.mta.hu

^b Department of Organic Chemistry, Faculty of Pharmacy, Semmelweis University, Hőgyes Endre u. 7., H-1092 Budapest, Hungary

^c Servier Research Institute of Medicinal Chemistry (SRIMC), Záhony utca 7., H-1031 Budapest, Hungary

^d Department of Pharmacognosy, Faculty of Pharmacy, Semmelweis University, Üllői út 26., H-1085 Budapest, Hungary

^e Institute of Materials and Environmental Chemistry, Research Center for Natural Sciences, Hungarian Academy of Sciences, Magyar Tudósok krt. 2., H-1117 Budapest, Hungary

^f Department of Medical Chemistry, University of Szeged, Dóm t. 8., H-6720 Szeged, Hungary

^g MTA SZTE Biomimetic Systems Research Group, Dóm t. 8., H-6720 Szeged, Hungary

^h MTA TTK Lendület Artificial Transporter Research Group, Institute of Materials and Environmental Chemistry, Research Center for Natural Sciences, Hungarian Academy of Sciences, Magyar Tudósok krt. 2., H-1117 Budapest, Hungary

Abstract

Enantiodiscriminative helix formation was observed for β-peptide H14 helices. This observation is caused by the synperiplanar orientation of H–O atoms which is more unfavorable than those for H–H interaction. The 1,2 H–O interaction leads to the destruction of the helical structure. The introduction of a double C–C bond in the backbone rules out helix formation.

Chemical Communications

Flow-chemistry enabled efficient synthesis of β-peptides: backbone topology vs. helix formation†

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Flow-chemistry enabled efficient synthesis of β-peptides: backbone topology vs. helix formation

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