Literature DB >> 15686913

Detection and control of aspartimide formation in the synthesis of cyclic peptides.

David Flora1, Huaping Mo, John P Mayer, M Amin Khan, Liang Z Yan.   

Abstract

Extensive two-dimensional NMR analysis was employed to characterize the structural identity of the macrocyclic peptide lactam and the imide analog, a major side reaction product when allyl ester was used to protect the side chain of aspartic acid. A straightforward protocol modification was developed to minimize aspartimide formation during the synthesis of cyclic peptides.

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Year:  2005        PMID： 15686913     DOI： 10.1016/j.bmcl.2004.12.025

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  6 in total

Review 1.  Cyclization-activated prodrugs.

Authors:  Paula Gomes; Nuno Vale; Rui Moreira
Journal:  Molecules       Date:  2007-11-12       Impact factor: 4.411

2.  Novel selective human melanocortin-3 receptor ligands: use of the 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one (Aba) scaffold.

Authors:  Steven Ballet; Alexander V Mayorov; Minying Cai; Dagmara Tymecka; Kevin B Chandler; Erin S Palmer; Karolien Van Rompaey; Aleksandra Misicka; Dirk Tourwé; Victor J Hruby
Journal:  Bioorg Med Chem Lett       Date:  2007-02-09       Impact factor: 2.823

3.  Substitution of arginine with proline and proline derivatives in melanocyte-stimulating hormones leads to selectivity for human melanocortin 4 receptor.

Authors:  Hongchang Qu; Minying Cai; Alexander V Mayorov; Paolo Grieco; Morgan Zingsheim; Dev Trivedi; Victor J Hruby
Journal:  J Med Chem       Date:  2009-06-25       Impact factor: 7.446

4.  Targeting cancer-specific glycans by cyclic peptide lectinomimics.

Authors:  Maria C Rodriguez; Austin B Yongye; Mihael Cudic; Karina Martinez Mayorga; Enbo Liu; Barbara M Mueller; Jon Ainsley; Tatyana Karabencheva-Christova; Christo Z Christov; Mare Cudic; Predrag Cudic
Journal:  Amino Acids       Date:  2017-09-11       Impact factor: 3.520

5.  Solid-phase synthesis of tailed cyclic RGD peptides using glutamic acid: unexpected glutarimide formation.

Authors:  Junmin Zhu; Roger E Marchant
Journal:  J Pept Sci       Date:  2008-06       Impact factor: 1.905

6.  Microwave-assisted solid-phase synthesis of side-chain to side-chain lactam-bridge cyclic peptides.

Authors:  Srinivasa R Tala; Sathya M Schnell; Carrie Haskell-Luevano
Journal:  Bioorg Med Chem Lett       Date:  2015-10-31       Impact factor: 2.823
  6 in total

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