Literature DB >> 19437515

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

Doralyn S Dalisay1, Tim Quach, Gillian N Nicholas, Tadeusz F Molinski.   

Abstract

A dramatic effect is observed when acyclic N-(2-naphthamides) of medium-chain 1-amino-2-methylalkanes are partially ordered with the help of liposomes: the Cotton effect arising from pi-pi* transitions of the terminal naphthamide chromophor is enormously enhanced. This effect was exploited to assign the configuration of new polyketide peroxides such as 1 from the sponge Plakortis halichondroides.

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Year:  2009        PMID： 19437515      PMCID： PMC2872062          DOI： 10.1002/anie.200900888

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 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

Review 2.  Nanomole-scale natural products discovery.

Authors:  Tadeusz F Molinski
Journal:  Curr Opin Drug Discov Devel       Date:  2009-03

3.  Genomic profiling of drug sensitivities via induced haploinsufficiency.

Authors:  G Giaever; D D Shoemaker; T W Jones; H Liang; E A Winzeler; A Astromoff; R W Davis
Journal:  Nat Genet       Date:  1999-03       Impact factor: 38.330

4.  Endoperoxide derivatives from marine organisms: 1,2-dioxanes of the plakortin family as novel antimalarial agents.

Authors:  Caterina Fattorusso; Giuseppe Campiani; Bruno Catalanotti; Marco Persico; Nicoletta Basilico; Silvia Parapini; Donatella Taramelli; Claudio Campagnuolo; Ernesto Fattorusso; Adriana Romano; Orazio Taglialatela-Scafati
Journal:  J Med Chem       Date:  2006-11-30       Impact factor: 7.446

5.  New cytotoxic peroxylactones from the marine sponge, Plakinastrella onkodes.

Authors:  P A Horton; R E Longley; M Kelly-Borges; O J McConnell; L M Ballas
Journal:  J Nat Prod       Date:  1994-10       Impact factor: 4.050

6.  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

7.  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

8.  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
  8 in total
  6 in total

1.  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

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

Authors:  Doralyn S Dalisay; Tim Quach; Tadeusz F Molinski
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

Review 3.  Microscale methodology for structure elucidation of natural products.

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

4.  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

5.  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

6.  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
  6 in total

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