Literature DB >> 20205426

Liposomal circular dichroism. Assignment of remote stereocenters in plakinic acids K and L from a Plakortis-Xestospongia sponge association.

Doralyn S Dalisay1, Tim Quach, Tadeusz F Molinski.   

Abstract

Two new omega-phenyl polyketide peroxides, plakinic acids K and L, were isolated from a two-sponge association of Plakortis halichondroides and Xestospongia deweerdtae. The absolute configurations of the remote dimethyl-branched stereocenters in plakinic acid K were assigned by degradation of plakinic acid K to a long-chain naphthamide and analysis by liposomal circular dichroism (L-CD) and comparison with synthetic standards.

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Year:  2010        PMID： 20205426      PMCID： PMC2846192          DOI： 10.1021/ol100249v

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


  7 in total

1.  Stereochemical assignment in acyclic lipids across long distance by circular dichroism: absolute stereochemistry of the aglycone of caminoside A.

Authors:  John B Macmillan; Roger G Linington; Raymond J Andersen; Tadeusz F Molinski
Journal:  Angew Chem Int Ed Engl       Date:  2004-11-12       Impact factor: 15.336

2.  New cyclic peroxides from the Philippine sponge Plakinastrella sp.

Authors:  A Qureshi; J Salvá; M K Harper; D J Faulkner
Journal:  J Nat Prod       Date:  1998-12       Impact factor: 4.050

3.  Stolonoxides E and F, cytotoxic metabolites from the marine ascidian Stolonica socialis.

Authors:  Fernando Reyes; Raquel Rodríguez-Acebes; Rogelio Fernández; Santiago Bueno; Andrés Francesch; Carmen Cuevas
Journal:  J Nat Prod       Date:  2010-01       Impact factor: 4.050

4.  Cytotoxic beta-carbolines and cyclic peroxides from the Palauan sponge Plakortis nigra.

Authors:  Joel S Sandler; Patrick L Colin; John N A Hooper; D John Faulkner
Journal:  J Nat Prod       Date:  2002-09       Impact factor: 4.050

5.  Amplification of the Cotton effect of a single chromophore through liposomal ordering-stereochemical assignment of plakinic acids I and J.

Authors:  Doralyn S Dalisay; Tim Quach; Gillian N Nicholas; Tadeusz F Molinski
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Long-range stereo-relay: relative and absolute configuration of 1,n-glycols from circular dichroism of liposomal porphyrin esters.

Authors:  John B MacMillan; Tadeusz F Molinski
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

7.  Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: synthesis and configurational assignment of plakinic acid A.

Authors:  Peng Dai; Tony K Trullinger; Xuejun Liu; Patrick H Dussault
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354
  7 in total
  8 in total

1.  Bioactive Cycloperoxides Isolated from the Puerto Rican Sponge Plakortis halichondrioides.

Authors:  Carlos Jiménez-Romero; Idelisse Ortiz; Jan Vicente; Brunilda Vera; Abimael D Rodríguez; Sangkil Nam; Richard Jove
Journal:  J Nat Prod       Date:  2010-10-05       Impact factor: 4.050

2.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

3.  Reassignment of the absolute configuration of plakinidone from the sponge consortium Plakortis halichondrioides-Xestospongia deweerdtae using a combination of synthesis and a chiroptical approach.

Authors:  Carlos Jiménez-Romero; Joanna E Rode; Abimael D Rodríguez
Journal:  Tetrahedron Asymmetry       Date:  2016-04-07

Review 4.  Microscale methodology for structure elucidation of natural products.

Authors:  Tadeusz F Molinski
Journal:  Curr Opin Biotechnol       Date:  2010-09-27       Impact factor: 9.740

5.  Temperature-dependent conformations of a membrane supported zinc porphyrin tweezer by 2D fluorescence spectroscopy.

Authors:  Julia R Widom; Wonbae Lee; Alejandro Perdomo-Ortiz; Dmitrij Rappoport; Tadeusz F Molinski; Alán Aspuru-Guzik; Andrew H Marcus
Journal:  J Phys Chem A       Date:  2013-03-29       Impact factor: 2.781

6.  Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers.

Authors:  Tadeusz F Molinski; Caroline D Broaddus; Brandon I Morinaka
Journal:  Mar Drugs       Date:  2017-12-20       Impact factor: 5.118

7.  Sponge symbioses between Xestospongia deweerdtae and Plakortis spp. are not motivated by shared chemical defense against predators.

Authors:  Micah Jaarsma Marty; Jan Vicente; Benjamin L Oyler; Allen Place; Russell T Hill
Journal:  PLoS One       Date:  2017-04-18       Impact factor: 3.240

Review 8.  A Decade of Antifungal Leads from Natural Products: 2010-2019.

Authors:  Mohammed Aldholmi; Pascal Marchand; Isabelle Ourliac-Garnier; Patrice Le Pape; A Ganesan
Journal:  Pharmaceuticals (Basel)       Date:  2019-12-12
  8 in total

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