Literature DB >> 20436939

Acyl radical insertion for the direct formation of new 7-substituted pterin analogs.

Jeff M Pruet1, Jon D Robertus, Eric V Anslyn.   

Abstract

A variety of pterin molecules were synthesized via an under-utilized acyl radical insertion, using aldehydes and alpha-keto esters as the acyl source. These reactions gave complete regiospecificity for the 7-isomer, with reaction times ranging in minutes, often with instantaneous product precipitation. This approach led to the construction of new pterin analogs unaccessable via traditional Friedel-Crafts acylation. The compounds were characterized by NMR spectroscopy and high-resolution mass spectroscopy.

Entities:  

Year:  2010        PMID: 20436939      PMCID: PMC2860152          DOI: 10.1016/j.tetlet.2010.03.008

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  1 in total

1.  Structure-based identification of a ricin inhibitor.

Authors:  X Yan; T Hollis; M Svinth; P Day; A F Monzingo; G W Milne; J D Robertus
Journal:  J Mol Biol       Date:  1997-03-14       Impact factor: 5.469

  1 in total
  5 in total

1.  Optimized 5-membered heterocycle-linked pterins for the inhibition of Ricin Toxin A.

Authors:  Jeff M Pruet; Ryota Saito; Lawrence A Manzano; Karl R Jasheway; Paul A Wiget; Ishan Kamat; Eric V Anslyn; Jon D Robertus
Journal:  ACS Med Chem Lett       Date:  2012-05-29       Impact factor: 4.345

2.  7-Substituted pterins provide a new direction for ricin A chain inhibitors.

Authors:  Jeff M Pruet; Karl R Jasheway; Lawrence A Manzano; Yan Bai; Eric V Anslyn; Jon D Robertus
Journal:  Eur J Med Chem       Date:  2011-05-20       Impact factor: 6.514

3.  Peptide-conjugated pterins as inhibitors of ricin toxin A.

Authors:  Ryota Saito; Jeff M Pruet; Lawrence A Manzano; Karl Jasheway; Arthur F Monzingo; Paul A Wiget; Ishan Kamat; Eric V Anslyn; Jon D Robertus
Journal:  J Med Chem       Date:  2012-12-19       Impact factor: 7.446

Review 4.  Structure-based design of ricin inhibitors.

Authors:  Karl Jasheway; Jeffrey Pruet; Eric V Anslyn; Jon D Robertus
Journal:  Toxins (Basel)       Date:  2011-10-13       Impact factor: 4.546

5.  Metal-free oxidative isocyanides insertion with aromatic aldehydes to aroylated N-heterocycles.

Authors:  Yimiao He; Xuelian Wang; Jun-An Xiao; Jinying Pang; Chunfang Gan; Yanmin Huang; Chusheng Huang
Journal:  RSC Adv       Date:  2018-01-15       Impact factor: 3.361

  5 in total

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