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Literature DB >> 21125121

Chlorosulfolipids: structure, synthesis, and biological relevance.

Abstract

Chlorosulfolipids have been isolated from freshwater algae and from toxic mussels. They appear to have a structural role in algal membranes and have been implicated in Diarrhetic Shellfish Poisoning. Further fascinating aspects of these compounds include their stereochemically complex polychlorinated structures and the resulting strong conformational biases, and their poorly understood (yet surely compelling) biosynthesis. Discussions of each of these topics and of efforts in structural and stereochemical elucidation and synthesis are the subject of this Highlight.

Entities: Chemical Disease Species

Mesh：

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Year: 2010 PMID： 21125121 PMCID： PMC3021328 DOI： 10.1039/c0np00044b

Source DB: PubMed Journal: Nat Prod Rep ISSN： 0265-0568 Impact factor: 13.423

30 in total

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Journal: Angew Chem Int Ed Engl Date: 2000-06-16 Impact factor: 15.336

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Journal: Biochemistry Date: 1974-08-13 Impact factor: 3.162

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Authors: Nobuaki Matsumori; Daisuke Kaneno; Michio Murata; Hideshi Nakamura; Kazuo Tachibana
Journal: J Org Chem Date: 1999-02-05 Impact factor: 4.354

4. Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.

Authors: Christian Nilewski; Roger W Geisser; Erick M Carreira
Journal: Nature Date: 2009-01-29 Impact factor: 49.962

5. Microbial sulpholipids: (R)-13-choro-1-(R)-14-docosanediol disulphate and polychlorosulpholipids in Ochromonas danica.

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Journal: Biochem J Date: 1969-07 Impact factor: 3.857

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Authors: Alban R Pereira; Tara Byrum; Grant M Shibuya; Christopher D Vanderwal; William H Gerwick
Journal: J Nat Prod Date: 2010-02-26 Impact factor: 4.050

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Journal: Biochemistry Date: 1969-07 Impact factor: 3.162

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Authors: J L Chen; P J Proteau; M A Roberts; W H Gerwick; D L Slate; R H Lee
Journal: J Nat Prod Date: 1994-04 Impact factor: 4.050

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Authors: J Elovson
Journal: Biochemistry Date: 1974-08-13 Impact factor: 3.162

10. Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.

Authors: Grant M Shibuya; Jacob S Kanady; Christopher D Vanderwal
Journal: J Am Chem Soc Date: 2008-08-22 Impact factor: 15.419

20 in total

1. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Authors: Jakub Saadi; Matsujiro Akakura; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2011-08-18 Impact factor: 15.419

2. Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

Authors: Susumu Oda; Hisashi Yamamoto
Journal: Org Lett Date: 2013-11-08 Impact factor: 6.005

3. Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors: Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2019-09-25 Impact factor: 15.419

4. Approaches to the chemical synthesis of the chlorosulfolipids.

Authors: Won-Jin Chung; Christopher D Vanderwal
Journal: Acc Chem Res Date: 2014-01-08 Impact factor: 22.384

5. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors: Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal: J Am Chem Soc Date: 2016-04-08 Impact factor: 15.419