Literature DB >> 20426464

Macrolactonization of peptide thioesters catalyzed by imidazole and its application in the synthesis of kahalalide B and analogues.

Yangmei Li1, Marc Giulionatti, Richard A Houghten.   

Abstract

The macrolactonization of peptide thioester to yield cyclic depsipeptides was developed using imidazole as a catalyst. This strategy was applied to the synthesis of kahalalide B and its analogues.

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Year:  2010        PMID： 20426464      PMCID： PMC3118573          DOI： 10.1021/ol100596p

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


  35 in total

1.  Modular Peptide Synthetases Involved in Nonribosomal Peptide Synthesis.

Authors:  Mohamed A. Marahiel; Torsten Stachelhaus; Henning D. Mootz
Journal:  Chem Rev       Date:  1997-11-10       Impact factor: 60.622

2.  Generality of peptide cyclization catalyzed by isolated thioesterase domains of nonribosomal peptide synthetases.

Authors:  R M Kohli; J W Trauger; D Schwarzer; M A Marahiel; C T Walsh
Journal:  Biochemistry       Date:  2001-06-19       Impact factor: 3.162

Review 3.  Technology evaluation: Kahalalide F, PharmaMar.

Authors:  Mark T Hamann
Journal:  Curr Opin Mol Ther       Date:  2004-12

4.  "Volatilizable" supports for high-throughput organic synthesis.

Authors:  Richard A Houghten; Yongping Yu
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

5.  Kahalalides: Bioactive Peptides from a Marine Mollusk Elysia rufescens and Its Algal Diet Bryopsis sp.(1).

Authors:  Mark T. Hamann; Clifton S. Otto; Paul J. Scheuer; D. Chuck Dunbar
Journal:  J Org Chem       Date:  1996-09-20       Impact factor: 4.354

6.  Macrolactamization versus macrolactonization: total synthesis of FK228, the depsipeptide histone deacetylase inhibitor.

Authors:  Shijun Wen; Graham Packham; A Ganesan
Journal:  J Org Chem       Date:  2008-12-05       Impact factor: 4.354

7.  Characterization of the surfactin synthetase C-terminal thioesterase domain as a cyclic depsipeptide synthase.

Authors:  Claire C Tseng; Steven D Bruner; Rahul M Kohli; Mohamed A Marahiel; Christopher T Walsh; Stephan A Sieber
Journal:  Biochemistry       Date:  2002-11-12       Impact factor: 3.162

8.  N-methylsansalvamide a peptide analogues. Potent new antitumor agents.

Authors:  Shouxin Liu; Wenxin Gu; Denise Lo; Xian-Zhong Ding; Michael Ujiki; Thomas E Adrian; Gerald A Soff; Richard B Silverman
Journal:  J Med Chem       Date:  2005-05-19       Impact factor: 7.446

9.  Intramolecular cross-linkage of lysozyme. Imidazole catalysis of the formation of the cross-link between lysine-13 (epsilon-amino) and leucine-129 (alpha-carboxyl) by carbodiimide reaction.

Authors:  H Yamada; R Kuroki; M Hirata; T Imoto
Journal:  Biochemistry       Date:  1983-09-13       Impact factor: 3.162

Review 10.  Marine peptides and related compounds in clinical trial.

Authors:  Diwan S Rawat; Mukesh C Joshi; Penny Joshi; Himanshu Atheaya
Journal:  Anticancer Agents Med Chem       Date:  2006-01       Impact factor: 2.505
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  3 in total

Review 1.  Contemporary strategies for peptide macrocyclization.

Authors:  Christopher J White; Andrei K Yudin
Journal:  Nat Chem       Date:  2011-06-23       Impact factor: 24.427

2.  Structure and Reactivity of Highly Twisted N-Acylimidazoles.

Authors:  Elizabeth A Stone; Brandon Q Mercado; Scott J Miller
Journal:  Org Lett       Date:  2019-03-12       Impact factor: 6.005

3.  The role of imidazole in peptide cyclization by transesterification: parallels to the catalytic triads of serine proteases.

Authors:  Kendall G Byler; Yangmei Li; Richard A Houghten; Karina Martinez-Mayorga
Journal:  Org Biomol Chem       Date:  2013-05-14       Impact factor: 3.876
  3 in total

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