Literature DB >> 20300486

Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary alpha-Amino Acids.

Carlos Cativiela1, Mario Ordóñez.   

Abstract

The most recent papers describing the stereoselective synthesis of cyclic quaternary alpha-amino acids are collected in this review. The diverse synthetic approaches are classified according to the size of the ring and taking into account the bond that is formed to complete the quaternary skeleton.

Entities:  

Year:  2009        PMID： 20300486      PMCID： PMC2839256          DOI： 10.1016/j.tetasy.2009.01.002

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN： 0957-4166


  165 in total

1.  Homogeneous Metathesis Polymerization by Well-Defined Group VI and Group VIII Transition-Metal Alkylidenes: Fundamentals and Applications in the Preparation of Advanced Materials.

Authors:  M R Buchmeiser
Journal:  Chem Rev       Date:  2000-04-12       Impact factor: 60.622

Review 2.  Natural occurrence, syntheses, and applications of cyclopropyl-group-containing alpha-amino acids. 2. 3,4- and 4,5-methanoamino acids.

Authors:  Farina Brackmann; Armin de Meijere
Journal:  Chem Rev       Date:  2007-10-18       Impact factor: 60.622

3.  Molecular modeling based approach to potent P2-P4 macrocyclic inhibitors of hepatitis C NS3/4A protease.

Authors:  Nigel J Liverton; M Katharine Holloway; John A McCauley; Michael T Rudd; John W Butcher; Steven S Carroll; Jillian DiMuzio; Christine Fandozzi; Kevin F Gilbert; Shi-Shan Mao; Charles J McIntyre; Kevin T Nguyen; Joseph J Romano; Mark Stahlhut; Bang-Lin Wan; David B Olsen; Joseph P Vacca
Journal:  J Am Chem Soc       Date:  2008-03-14       Impact factor: 15.419

Review 4.  Aldose reductase inhibitors: a potential new class of agents for the pharmacological control of certain diabetic complications.

Authors:  P F Kador; J H Kinoshita; N E Sharpless
Journal:  J Med Chem       Date:  1985-07       Impact factor: 7.446

5.  A theoretical study of pentacyclo-undecane cage peptides of the type [Ac-X-Y-NHMe].

Authors:  Krishna Bisetty; Francesc J Corcho; Josep Canto; Hendrik G Kruger; Juan J Perez
Journal:  J Pept Sci       Date:  2006-02       Impact factor: 1.905

6.  Design and synthesis of APTCs (aminopyrrolidinetricarboxylic acids): identification of a new group III metabotropic glutamate receptor selective agonist.

Authors:  Stephan Schann; Christel Menet; Paul Arvault; Géraldine Mercier; Mélanie Frauli; Stanislas Mayer; Nadia Hubert; Nicolas Triballeau; Hugues-Olivier Bertrand; Francine Acher; Pascal Neuville
Journal:  Bioorg Med Chem Lett       Date:  2006-07-07       Impact factor: 2.823

7.  Highly enantioselective electrophilic amination and michael addition of cyclic beta-ketoesters induced by lanthanides and (S,S)-ip-pybox: the mechanism.

Authors:  Josep Comelles; Alex Pericas; Marcial Moreno-Mañas; Adelina Vallribera; Galí Drudis-Solé; Agusti Lledos; Teodor Parella; Anna Roglans; Santiago García-Granda; Laura Roces-Fernández
Journal:  J Org Chem       Date:  2007-02-22       Impact factor: 4.354

8.  Synthesis, in vitro pharmacology, structure-activity relationships, and pharmacokinetics of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent and selective group II metabotropic glutamate receptor antagonists.

Authors:  Atsuro Nakazato; Kazunari Sakagami; Akito Yasuhara; Hiroshi Ohta; Ryoko Yoshikawa; Manabu Itoh; Masato Nakamura; Shigeyuki Chaki
Journal:  J Med Chem       Date:  2004-08-26       Impact factor: 7.446

9.  Novel, highly potent aldose reductase inhibitors: (R)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4- tetrahydropyrrolo[1,2-a]pyrazine -4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone (AS-3201) and its congeners.

Authors:  T Negoro; M Murata; S Ueda; B Fujitani; Y Ono; A Kuromiya; M Komiya; K Suzuki; J Matsumoto
Journal:  J Med Chem       Date:  1998-10-08       Impact factor: 7.446

10.  Synthesis, antiviral activity, and conformational studies of a P3 aza-peptide analog of a potent macrocyclic tripeptide HCV protease inhibitor.

Authors:  John T Randolph; Xiaolin Zhang; Peggy P Huang; Larry L Klein; Kevin A Kurtz; Alex K Konstantinidis; Wenping He; Warren M Kati; Dale J Kempf
Journal:  Bioorg Med Chem Lett       Date:  2008-02-26       Impact factor: 2.823
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  15 in total

1.  NCAD, a database integrating the intrinsic conformational preferences of non-coded amino acids.

Authors:  Guillem Revilla-López; Juan Torras; David Curcó; Jordi Casanovas; M Isabel Calaza; David Zanuy; Ana I Jiménez; Carlos Cativiela; Ruth Nussinov; Piotr Grodzinski; Carlos Alemán
Journal:  J Phys Chem B       Date:  2010-06-03       Impact factor: 2.991

2.  Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

Authors:  Hideyuki Konishi; Tin Yiu Lam; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

3.  Application of a new chiral phosphepine to the catalytic asymmetric synthesis of highly functionalized cyclopentenes that bear an array of heteroatom-substituted quaternary stereocenters.

Authors:  Yuji Fujiwara; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2011-07-18       Impact factor: 15.419

4.  Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine.

Authors:  Cedric L Hugelshofer; Kevin T Mellem; Andrew G Myers
Journal:  Org Lett       Date:  2013-06-07       Impact factor: 6.005

5.  A Protocol for the Design of Protein and Peptide Nanostructure Self-Assemblies Exploiting Synthetic Amino Acids.

Authors:  Nurit Haspel; Jie Zheng; Carlos Aleman; David Zanuy; Ruth Nussinov
Journal:  Methods Mol Biol       Date:  2017

6.  Catalytic, Enantioselective α-Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation.

Authors:  Sri Krishna Nimmagadda; Mingyu Liu; Malkanthi K Karunananda; De-Wei Gao; Omar Apolinar; Jason S Chen; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-27       Impact factor: 15.336

7.  Ethyl 1-formamido-4-oxo-2,6-diphenyl-cyclo-hexa-necarboxyl-ate.

Authors:  Dawei Zhang; Xianxiu Xu; Qun Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-15

8.  Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

Authors:  Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2019-07-29       Impact factor: 4.036

9.  Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.

Authors:  John M Curto; Joshua S Dickstein; Simon Berritt; Marisa C Kozlowski
Journal:  Org Lett       Date:  2014-03-25       Impact factor: 6.005

10.  α-Allyl-α-aryl α-amino esters in the asymmetric synthesis of acyclic and cyclic amino acid derivatives by alkene metathesis.

Authors:  John M Curto; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2014-05-14       Impact factor: 4.354
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