Nicola Landoni

University of Milan

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Giordano Lesma

University of Milan

Alessandro Sacchetti

Politecnico di Milano

Alessandra Silvani

University of Milan

Tullio Pilati

Politecnico di Milano

T. Pilati

Institute of Molecular Science and Technologies

Andrea Kövér

Universidad Rovira i Virgili

Maria Pérez

Universitat de Barcelona

Jesús Bautista

Universitat de Barcelona

O. Lozano

Centro Nacional de Investigaciones Científicas

Mercedes Amat

Universitat de Barcelona

Cooperative Institutions

Universitat de Barcelona

Institute of Molecular Science and Technologies

University of Milan

Mylan (Switzerland)

Milano University Press

Politecnico di Milano

Institute for Biomedicine

University of Lisbon

Mylan (South Africa)

Institut de Ciència de Materials de Barcelona

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CCDC 734071: Experimental Crystal Structure Determination

The Cambridge Structural Database (2010)

Giordano Lesma Nicola Landoni T. Pilati A. Sacchetti Alessandra Silvani

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccsmvqy

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The spiropiperidine-3,3′-oxindole scaffold: a type II β-turn peptide isostere

Tetrahedron (2010)

Giordano Lesma Nicola Landoni Alessandro Sacchetti Alessandra Silvani

Enantiopure drug

Oxindole

Isostere

Turn (biochemistry)

Ring-Closing Metathesis

Lactam

10.1016/j.tet.2010.04.077

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Citations (42)

Ttrahydroisoquiolie-based peptidomimetics mimickig reverse turn secondary structures

Nicola Landoni Giordano Lesma Alessandro Sacchetti Alessandra Silvani

Peptidomimetic

Turn (biochemistry)

Source

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Grignard Addition to Imines Derived from Isatine: A Method for the Asymmetric Synthesis of Quaternary 3-Aminooxindoles

The Journal of Organic Chemistry (2009)

Giordano Lesma Nicola Landoni Tullio Pilati Alessandro Sacchetti Alessandra Silvani

Addition of Grignard reagents to chiral imines derived from isatine afforded chiral, optically enriched 3-substituted 3-aminooxindoles in satisfactory yields and diastereoisomeric ratios. A general protocol is described for the addition of alkyl, alkenyl, and aryl Grignard reagents. In one case, the absolute configuration at C3 was determined and the selective N-deprotection was described, enabling further synthetic transformations of the reaction product.

Absolute Configuration

Grignard reagent

Grignard reaction

10.1021/jo900623c

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Citations (95)

A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines

Tetrahedron Asymmetry (2007)

Giordano Lesma Alessia Colombo Nicola Landoni Alessandro Sacchetti Alessandra Silvani

Hydroxymethyl

Dihydroxylation

Piperidine

Candida antarctica

10.1016/j.tetasy.2007.07.017

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Citations (24)

Tetrahydroisoquinoline-Based Spirocyclic Lactam as a Type II′ β-Turn Inducing Peptide Mimetic

The Journal of Organic Chemistry (2009)

Giordano Lesma Nicola Landoni Tullio Pilati Alessandro Sacchetti Alessandra Silvani

We present here spirocyclic lactam derivatives, embodying D-Phe and L-Ala amino acids as the central core and acting as tetrapeptide and hexapeptide mimetics. An efficient route for their synthesis is demonstrated by using the strategic combination of Seebach's self-reproduction of chirality chemistry and the Pictet-Spengler condensation as key steps. The conformational behavior of peptide mimetics was investigated by molecular modeling, X-ray crystallography, NMR (solvent and temperature dependence), IR spectroscopy, and circular dichroism. All data suggest very stable and highly predictable type II' beta-turn conformations.

Tetrapeptide

Lactam

Chirality

Turn (biochemistry)

Tetrahydroisoquinoline

10.1021/jo901480d

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Citations (22)

Pyrroloisoquinoline-Based Tetrapeptide Analogues Mimicking Reverse-Turn Secondary Structures

The Journal of Organic Chemistry (2007)

Nicola Landoni Giordano Lesma Alessandro Sacchetti Alessandra Silvani

New pyrroloisoquinoline-based tetrapeptides were synthesized in enantiomerically pure form, and their conformational features were studied by NMR, IR, and molecular-modeling techniques. The presence of a reverse turn was observed in both structures, with the C1 stereochemistry playing a central role in determining stable conformations. In particular, all of the analyses led to the conclusion that a type II' beta-turn is mostly stabilized in tetrapeptide mimic 3a, while a typical inverse gamma-turn geometry is revealed for the diastereoisomer 3b.

Tetrapeptide

Turn (biochemistry)

Diastereomer

Molecular model

10.1021/jo701581j

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Citations (24)

Synthesis and Conformational Analysis of Tetrahydroisoquinoline-based Pseudopeptides as Suitable Reverse Turn Mimetics

Giordano Lesma Alessandra Silvani Nicola Landoni Alessandro Sacchetti

Turn (biochemistry)

Source

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Synthesis of a tetrahydroimidazo- [2’,1’:2,3]thiazolo[5,4-c]pyridine derivative with Met inhibitory activity

ARKIVOC (2009)

Mercedes Amat Andrea Kövér Danica Jokic O. Lozano Maria Pérez

A straightforward synthesis of the Met antagonist JLK1360 involving an alkylationcyclocondensation process using aminothiazole 1 and nitrophenacyl bromide 2, reduction of the nitro group, and coupling of the resulting tetracyclic aniline 5 with an appropriate N-acyl alanine derivative, is reported.

Derivative (finance)

10.3998/ark.5550190.0011.313

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Citations (1)

ChemInform Abstract: Grignard Addition to Imines Derived from Isatin: A Method for the Asymmetric Synthesis of Quaternary 3‐Aminooxindoles.

ChemInform (2009)

Giordano Lesma Nicola Landoni Tullio Pilati Alessandro Sacchetti Alessandra Silvani

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Isatin

10.1002/chin.200944120

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