Synthesis of photoactivatable analogues of lysophosphatidic acid and covalent labeling of plasma proteins

Zaiguo Li, Daniel L. Baker, Gabor Tigyi, Robert Bittman

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Lysophosphatidic acids hearing a benzophenone group in either the sn-1 or sn-2 chain of an oleoyl-type ester or oleyl-type ether chain and 32 P in the phosphate group were synthesized. The benzophenone moiety was introduced by selective hydroboration of the double bond of enyne 11 at low temperature, followed by a Suzuki reaction with 4-bromobenzophenone. The key intermediates for the preparation of ester-linked lysophosphatidic acid (LPA) 1 and 3 were obtained in one pot by a modified DIBAL-H reduction of orthoformate intermediate 22. These probes were shown to covalently modify a single protein target in rat plasma containing albumin and several protein targets in rat plasma containing a low level of albumin.

Original languageEnglish (US)
Pages (from-to)629-635
Number of pages7
JournalJournal of Organic Chemistry
Volume71
Issue number2
DOIs
StatePublished - Jan 20 2006

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Labeling
Rats
Blood Proteins
Albumins
Esters
Lysophospholipids
Plasmas
Audition
Ether
Proteins
Phosphates
Temperature
lysophosphatidic acid
benzophenone
diisobutylaluminum

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Synthesis of photoactivatable analogues of lysophosphatidic acid and covalent labeling of plasma proteins. / Li, Zaiguo; Baker, Daniel L.; Tigyi, Gabor; Bittman, Robert.

In: Journal of Organic Chemistry, Vol. 71, No. 2, 20.01.2006, p. 629-635.

Research output: Contribution to journalArticle

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