Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar αVβ3 integrin ligand

Lorenzo Sernissi; Luciano Ricci; Dina Scarpi; Francesca Bianchini; Daniela Arosio; Alessandro Contini; Ernesto G. Occhiato

doi:10.1039/c8ob00534f

Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar αVβ3 integrin ligand

Organic & Biomolecular Chemistry ◽

10.1039/c8ob00534f ◽

2018 ◽

Vol 16 (18) ◽

pp. 3402-3414 ◽

Cited By ~ 3

Author(s):

Lorenzo Sernissi ◽

Luciano Ricci ◽

Dina Scarpi ◽

Francesca Bianchini ◽

Daniela Arosio ◽

...

Keyword(s):

Amino Acids ◽

Αvβ3 Integrin ◽

Integrin Ligand ◽

Constrained Amino Acids

A stereodivergent preparation of trans and cis-5-aminopipecolic acids (5-APAs) was developed to obtain constrained amino acids useful for peptidomimetics.

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Total asymmetric synthesis of highly constrained amino acids β-isopropyl-2′,6′-dimethyl-tyrosines

Tetrahedron Letters ◽

10.1016/s0040-4039(97)01094-0 ◽

1997 ◽

Vol 38 (29) ◽

pp. 5135-5138 ◽

Cited By ~ 11

Author(s):

Yinglin Han ◽

Subo Liao ◽

Wei Qiu ◽

Chaozhong Cai ◽

Victor J. Hruby

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Constrained Amino Acids

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Entry to New Conformationally Constrained Amino Acids. First Synthesis of 3-Unsubstituted 4-Alkyl-4-carboxy-2-azetidinone Derivatives via an IntramolecularNα-Cα-Cyclization Strategy

The Journal of Organic Chemistry ◽

10.1021/jo015559b ◽

2001 ◽

Vol 66 (10) ◽

pp. 3538-3547 ◽

Cited By ~ 55

Author(s):

Guillermo Gerona-Navarro ◽

Maria Angeles Bonache ◽

Rosario Herranz ◽

Maria Teresa García-López ◽

Rosario González-Muñiz

Keyword(s):

Amino Acids ◽

Conformationally Constrained ◽

Conformationally Constrained Amino Acids ◽

Constrained Amino Acids

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Flower-like Mn-Doped Magnetic Nanoparticles Functionalized with αvβ3-Integrin-Ligand to Efficiently Induce Intracellular Heat after Alternating Magnetic Field Exposition, Triggering Glioma Cell Death

ACS Applied Materials & Interfaces ◽

10.1021/acsami.9b08318 ◽

2019 ◽

Vol 11 (30) ◽

pp. 26648-26663 ◽

Cited By ~ 12

Author(s):

S. Del Sol-Fernández ◽

Y. Portilla-Tundidor ◽

L. Gutiérrez ◽

O. F. Odio ◽

E. Reguera ◽

...

Keyword(s):

Magnetic Field ◽

Cell Death ◽

Magnetic Nanoparticles ◽

Glioma Cell ◽

Alternating Magnetic Field ◽

Αvβ3 Integrin ◽

Integrin Ligand ◽

Mn Doped

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Conformationally Constrained Amino Acids in Peptide Design

SSRN Electronic Journal ◽

10.2139/ssrn.2767061 ◽

2016 ◽

Author(s):

V.S. Saravana Mani ◽

R. Narayanasamy

Keyword(s):

Amino Acids ◽

Peptide Design ◽

Conformationally Constrained ◽

Conformationally Constrained Amino Acids ◽

Constrained Amino Acids

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ChemInform Abstract: Constrained Amino Acids, an Approach to the Synthesis of 3-Substituted Prolines.

ChemInform ◽

10.1002/chin.199637273 ◽

2010 ◽

Vol 27 (37) ◽

pp. no-no

Author(s):

P. P. WAID ◽

G. A. FLYNN ◽

E. W. HUBER ◽

J. S. SABOL

Keyword(s):

Amino Acids ◽

Constrained Amino Acids

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Incorporation of Conformationally Constrained ?-Amino Acids into Peptides

Journal of Peptide Science ◽

10.1002/1099-1387(200007)6:7<301::aid-psc260>3.0.co;2-1 ◽

2000 ◽

Vol 6 (7) ◽

pp. 301-313 ◽

Cited By ~ 26

Author(s):

Michael North

Keyword(s):

Amino Acids ◽

Conformationally Constrained ◽

Conformationally Constrained Amino Acids ◽

Constrained Amino Acids

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ChemInform Abstract: Application of 7-endo, 8-endo and 9-endo Radical Cyclizations to the Synthesis of Conformationally Constrained Amino Acids and Comparison with the Corresponding Heck Reactions.

ChemInform ◽

10.1002/chin.199733208 ◽

2010 ◽

Vol 28 (33) ◽

pp. no-no

Author(s):

S. E. GIBSON ◽

N. GUILLO ◽

M. J. TOZER

Keyword(s):

Amino Acids ◽

Radical Cyclizations ◽

Heck Reactions ◽

Conformationally Constrained ◽

Conformationally Constrained Amino Acids ◽

Constrained Amino Acids

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Substitution of the Side-Chain-Constrained Amino Acids β-Methyl-2‘,6‘-Dimethyl-4‘-Methoxytyrosine in Position 2 of a Bicyclic Oxytocin Analogue Provides Unique Insights into the Bioactive Topography of Oxytocin Antagonists

Journal of the American Chemical Society ◽

10.1021/ja980848b ◽

1998 ◽

Vol 120 (29) ◽

pp. 7393-7394 ◽

Cited By ~ 16

Author(s):

Subo Liao ◽

Mark D. Shenderovich ◽

Zhigang Zhang ◽

Lenka Maletinska ◽

Jirina Slaninova ◽

...

Keyword(s):

Amino Acids ◽

Side Chain ◽

Oxytocin Antagonists ◽

Constrained Amino Acids

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ChemInform Abstract: Conformationally Constrained Amino Acids: A Convenient Approach to cis-2,3-Methano-GABAs.

ChemInform ◽

10.1002/chin.199929193 ◽

2010 ◽

Vol 30 (29) ◽

pp. no-no

Author(s):

Luca Forti ◽

Franco Ghelfi ◽

Stefano Levizzani ◽

Ugo M. Pagnoni

Keyword(s):

Amino Acids ◽

Conformationally Constrained ◽

Convenient Approach ◽

Conformationally Constrained Amino Acids ◽

Constrained Amino Acids

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Synthesis of oxytocin antagonists containing conformationally constrained amino acids in position 2

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/s0960-894x(99)00041-4 ◽

1999 ◽

Vol 9 (5) ◽

pp. 667-672 ◽

Cited By ~ 17

Author(s):

Gábor K. Tóth ◽

Krisztina Bakos ◽

Botond Penke ◽

Imre Pávó ◽

Csaba Varga ◽

...

Keyword(s):

Amino Acids ◽

Conformationally Constrained ◽

Oxytocin Antagonists ◽

Conformationally Constrained Amino Acids ◽

Constrained Amino Acids

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