Literature DB >> 16048348

Concise synthesis of all stereoisomers of beta-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A.

Angela Zampella1, Rosa D'Orsi, Valentina Sepe, Agostino Casapullo, Maria Chiara Monti, Maria Valeria D'Auria.   

Abstract

All stereoisomers of beta-methoxytyrosine (beta-OMeTyr), a stereo-undefined component of callipeltin A, were synthesized from L- and D-tyrosine. The stereochemistry of beta-OMeTyr in callipeltin A was determined to be 2R,3R by an oxidative procedure and Marfey's analysis. [structure: see text]

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Year:  2005        PMID： 16048348     DOI： 10.1021/ol0513600

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


  9 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.  Solid-phase synthesis and configurational reassigment of callipeltin E. Implications for the structures of callipeltins A and B.

Authors:  Selçuk Calimsiz; Angel I Morales Ramos; Mark A Lipton
Journal:  J Org Chem       Date:  2006-08-18       Impact factor: 4.354

3.  Expedient synthesis of threo-beta-hydroxy-alpha-amino acid derivatives: phenylalanine, tyrosine, histidine, and tryptophan.

Authors:  David Crich; Abhisek Banerjee
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

4.  Stellettapeptins A and B, HIV-inhibitory cyclic depsipeptides from the marine sponge Stelletta sp.

Authors:  Hee Jae Shin; Mohammad A Rashid; Laura K Cartner; Heidi R Bokesch; Jennifer A Wilson; James B McMahon; Kirk R Gustafson
Journal:  Tetrahedron Lett       Date:  2015-07-08       Impact factor: 2.415

5.  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

6.  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

7.  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

8.  Swinhopeptolides A and B: Cyclic Depsipeptides from the Sponge Theonella swinhoei That Inhibit Ras/Raf Interaction.

Authors:  Chang-Kwon Kim; Dongdong Wang; Heidi R Bokesch; Richard W Fuller; Emily Smith; Curtis J Henrich; David E Durrant; Deborah K Morrison; Carole A Bewley; Kirk R Gustafson
Journal:  J Nat Prod       Date:  2020-03-19       Impact factor: 4.050

Review 9.  Natural products from the Lithistida: a review of the literature since 2000.

Authors:  Priscilla L Winder; Shirley A Pomponi; Amy E Wright
Journal:  Mar Drugs       Date:  2011-12-15       Impact factor: 6.085
  9 in total

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