Literature DB >> 12492322

Diastereoselective synthesis of all stereoisomers of beta-methoxytyrosine, a component of papuamides.

Naoki Okamoto1, Osamu Hara, Kazuishi Makino, Yasumasa Hamada.   

Abstract

beta-Methoxytyrosine (beta-OMeTyr) is a stereoundefined component of papuamides A and B, novel cyclodepsipeptides, with anti-HIV and cytotoxic activities. For structural determination and total synthesis of papuamides, all stereoisomers of beta-OMeTyr were stereoselectively prepared from (S)- and (R)-serine, respectively.

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Year:  2002        PMID： 12492322     DOI： 10.1021/jo0258352

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  Enantio- and diastereoselective synthesis of (R,R)-beta-methoxytyrosine.

Authors:  David C Cranfill; Mark A Lipton
Journal:  Org Lett       Date:  2007-08-03       Impact factor: 6.005

2.  Complete stereochemistry of neamphamide A and absolute configuration of the beta-methoxytyrosine residue in papuamide B.

Authors:  Naoya Oku; Ravi Krishnamoorthy; Alan G Benson; Robert L Ferguson; Mark A Lipton; Lawrence R Phillips; Kirk R Gustafson; James B McMahon
Journal:  J Org Chem       Date:  2005-08-19       Impact factor: 4.354

3.  Solid-phase total synthesis and structure proof of callipeltin B.

Authors:  Ravi Krishnamoorthy; Leslie D Vazquez-Serrano; Jeffrey A Turk; Jennifer A Kowalski; Alan G Benson; Nneka T Breaux; Mark A Lipton
Journal:  J Am Chem Soc       Date:  2006-12-06       Impact factor: 15.419

4.  Theopapuamide, a cyclic depsipeptide from a Papua New Guinea lithistid sponge Theonella swinhoei.

Authors:  Anokha S Ratnayake; Tim S Bugni; Xidong Feng; Mary Kay Harper; Jack J Skalicky; Kaleem A Mohammed; Cynthia D Andjelic; Louis R Barrows; Chris M Ireland
Journal:  J Nat Prod       Date:  2006-11       Impact factor: 4.050

Review 5.  Marine Cyclic Peptides: Antimicrobial Activity and Synthetic Strategies.

Authors:  Ricardo Ribeiro; Eugénia Pinto; Carla Fernandes; Emília Sousa
Journal:  Mar Drugs       Date:  2022-06-15       Impact factor: 6.085

6.  Cyclodepsipeptides from marine sponges: natural agents for drug research.

Authors:  Gowri Shankar Bagavananthem Andavan; Rosa Lemmens-Gruber
Journal:  Mar Drugs       Date:  2010-03-22       Impact factor: 5.118

7.  Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography-electrospray ionization mass spectrometry.

Authors:  Sonja Hess; Kirk R Gustafson; Dennis J Milanowski; Edgardo Alvira; Mark A Lipton; Lewis K Pannell
Journal:  J Chromatogr A       Date:  2004-05-07       Impact factor: 4.759

8.  Stereocontrolled synthesis of syn-β-Hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide.

Authors:  Ian B Seiple; Jaron A M Mercer; Robin J Sussman; Ziyang Zhang; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336
  8 in total

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