Synthesis 2006(7): 1133-1140  
DOI: 10.1055/s-2006-926370
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Functionalized Azabicycloalkane Amino Acids as Dipeptide Mimics

Leonardo Manzoni*a, Laura Belvisib, Eliana DiCarloc, Alessandra Fornia, Donatella Invernizzib, Carlo Scolastico*b
a C.N.R., Istituto di Scienze e Tecnologie Molecolari (ISTM) and Centro Interdisciplinare Studi biomolecolari e applicazioni Industriali (CISI), Via Venezian 21, 20133 Milan, Italy
b Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano and Centro Interdisciplinare Studi biomolecolari e applicazioni­ Industriali (CISI), Via Venezian 21, 20133 Milan, Italy
c Centro Interdisciplinare Studi biomolecolari e applicazioni Industriali (CISI), Via Venezian 21, 20133 Milan, Italy
Fax: +39(0250)314072; e-Mail: leonardo.manzoni@istm.cnr.it; e-Mail: carlo.scolastico@unimi.it;
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Publikationsverlauf

Received 21 October 2005
Publikationsdatum:
08. März 2006 (online)

Abstract

Functionalized bicyclic lactams serve as building blocks for the synthesis of conformationally constrained peptides. A route to these building blocks is described based on the stereoselective alkylation of an appropriate azabicycloalkane; all possible diaste­reo­isomers can be obtained stereoselectively.

13

X-ray data of isomer 13b were collected on a Bruker Smart Apex CCD area detector using graphite-monochromated Mo-Kα radiation (λ = 0.71073 Å). Data reductions were made using SAINT programs. The structures were solved by SIR-92 and refined on F 2 by full-matrix least-squares using SHELXL-97. Crystal data: C27H34N2O3, M r = 434.56, colorless prism 0.34 × 0.16 × 0.13 mm, orthorhombic, P212121, a = 10.3435 (9), b = 13.0923 (12), c = 17.8267 (15) Å, V = 2414.1 (4) Å3, Z = 4, T = 150 (2) K, µ = 0.078 mm-1; 13026 measured reflections, 4274 independent reflections, 2859 reflections with I>2σ(I), 3.86<2θ <64.26°, R int = 0.041. Refinement on 4274 reflections, 391 parameters. Final R = 0.0424, wR = 0.0801 for data with F 2>2σ(F 2), (Δ/σ)max = 0.001, Δρ max = 0.29, Δρ min = -0.20 eÅ-3. Tables of atomic coordinates, anisotropic thermal parameters, bond lengths and angles of isomer 13b may be obtained free of charge from The Director CCDC, 12 Union Road, Cambridge CB2 1 EZ, UK, on quoting the deposition number CCDC 285315, the names of the authors, and the journal citation [fax:+44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk; web site: http://www.ccdc.cam.ac.uk].