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Literature DB >> 17132003

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

Ravi Krishnamoorthy¹, Leslie D Vazquez-Serrano, Jeffrey A Turk, Jennifer A Kowalski, Alan G Benson, Nneka T Breaux, Mark A Lipton.

Abstract

The cytotoxic, cyclic heptadepsipeptide, natural product callipeltin B was synthesized on a solid-phase support in 15% overall yield. Comparison of the 1H NMR spectra of three synthetic isomers with those of callipeltin B confirmed the configurational reassignment of its threonine residues as d-allothreonine and the assignment of the configuration of its beta-methoxytyrosine residue as (2R,3R).

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17132003 PMCID： PMC2582558 DOI： 10.1021/ja0666250

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

5 in total

1. 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

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

Authors: Angela Zampella; Rosa D'Orsi; Valentina Sepe; Agostino Casapullo; Maria Chiara Monti; Maria Valeria D'Auria
Journal: Org Lett Date: 2005-08-04 Impact factor: 6.005

3. 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

4. Stereoselective synthesis of four stereoisomers of beta-methoxytyrosine, a component of callipeltin A.

Authors: Darren B Hansen; Xiaobo Wan; Patrick J Carroll; Madeleine M Joullié
Journal: J Org Chem Date: 2005-04-15 Impact factor: 4.354

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

Authors: Naoki Okamoto; Osamu Hara; Kazuishi Makino; Yasumasa Hamada
Journal: J Org Chem Date: 2002-12-27 Impact factor: 4.354

5 in total

8 in total

Review 1. Nonproteinogenic amino acid building blocks for nonribosomal peptide and hybrid polyketide scaffolds.

Authors: Christopher T Walsh; Robert V O'Brien; Chaitan Khosla
Journal: Angew Chem Int Ed Engl Date: 2013-05-31 Impact factor: 15.336

2. 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

3. Synthesis of complex head-to-side-chain cyclodepsipeptides.

Authors: Marta Pelay-Gimeno; Fernando Albericio; Judit Tulla-Puche
Journal: Nat Protoc Date: 2016-09-15 Impact factor: 13.491

4. Synthesis and cytotoxicity of desmethoxycallipeltin B: lack of a quinone methide for the cytotoxicity of callipeltin B.

Authors: Ravi Krishnamoorthy; Brooke L Richardson; Mark A Lipton
Journal: Bioorg Med Chem Lett Date: 2007-07-07 Impact factor: 2.823

Review 8. Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge.

Authors: Guillermo Tarazona; Rogelio Fernández; Marta Pérez; Ramón E Millán; Carlos Jiménez; Jaime Rodríguez; Carmen Cuevas
Journal: J Nat Prod Date: 2022-03-02 Impact factor: 4.803