Literature DB >> 16671792

Dipeptide analogues containing 4-ethoxy-3-pyrrolin-2-ones.

Masood Hosseini1, Henriette Kringelum, Anthony Murray, Janne E Tønder.   

Abstract

[reaction: see text] Pyrrolidine-2,4-diones (1) are naturally occurring analogues of amino acids. We herein present a facile synthesis of N-acylated, O-alkylated pyrrolin-2-ones (2) in high yield and excellent enantiopurity. Molecular mechanics calculations suggest that the resulting dipeptide analogues adopt a linear, extended conformation.

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Year:  2006        PMID： 16671792     DOI： 10.1021/ol060500i

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Concise total synthesis of sintokamides A, B, and E by a unified, protecting-group-free strategy.

Authors:  Zhenhua Gu; Armen Zakarian
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-10       Impact factor: 15.336

2.  Synthesis of Chiral Tetramic Acids: Preparation of (S)-5-Benzylpyrrolidine-2,4-dione from L-Phenylalanine Methyl Ester Hydrochloride.

Authors:  Kyle M Lambert; Austin W Medley; Amy C Jackson; Lauren E Markham; John L Wood
Journal:  Organic Synth       Date:  2019

3.  Symplocin A, a linear peptide from the Bahamian cyanobacterium Symploca sp. Configurational analysis of N,N-dimethylamino acids by chiral-phase HPLC of naphthacyl esters.

Authors:  Tadeusz F Molinski; Kirk A Reynolds; Brandon I Morinaka
Journal:  J Nat Prod       Date:  2012-02-23       Impact factor: 4.050

4.  Expanding the scope of oligo-pyrrolinone-pyrrolidines as protein-protein interface mimics.

Authors:  Arjun Raghuraman; Dongyue Xin; Lisa M Perez; Kevin Burgess
Journal:  J Org Chem       Date:  2013-05-08       Impact factor: 4.354

5.  Pyrrolinone-pyrrolidine oligomers as universal peptidomimetics.

Authors:  Arjun Raghuraman; Eunhwa Ko; Lisa M Perez; Thomas R Ioerger; Kevin Burgess
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

6.  Discovery and Total Synthesis of Doscadenamide A: A Quorum Sensing Signaling Molecule from a Marine Cyanobacterium.

Authors:  Xiao Liang; Susan Matthew; Qi-Yin Chen; Jason C Kwan; Valerie J Paul; Hendrik Luesch
Journal:  Org Lett       Date:  2019-08-15       Impact factor: 6.005

7.  A general diastereoselective catalytic vinylogous aldol reaction among tetramic acid-derived pyrroles.

Authors:  Jonathan G David; Wen-Ju Bai; Marisa G Weaver; Thomas R R Pettus
Journal:  Org Lett       Date:  2014-08-13       Impact factor: 6.005

8.  Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A.

Authors:  Alessia Caso; Alfonso Mangoni; Gennaro Piccialli; Valeria Costantino; Vincenzo Piccialli
Journal:  ACS Omega       Date:  2017-04-17

9.  Synthesis of a leopolic acid-inspired tetramic acid with antimicrobial activity against multidrug-resistant bacteria.

Authors:  Luce Mattio; Loana Musso; Leonardo Scaglioni; Andrea Pinto; Piera Anna Martino; Sabrina Dallavalle
Journal:  Beilstein J Org Chem       Date:  2018-09-24       Impact factor: 2.883
  9 in total

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