Synthesis of fluorescent phosphatidylinositols using a novel inositol H- phosphonate

Lawrence W. Leung; Catherine Vilchèze; Robert Bittman

doi:10.1016/S0040-4039(98)00418-3

Synthesis of fluorescent phosphatidylinositols using a novel inositol H- phosphonate

Lawrence W. Leung
, Catherine Vilchèze
, Robert Bittman

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Coupling of 1,2-diradyl-sn-glycerol 5 with the novel inositol H- phosphonate derivative, 6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol H-phosphonate (3), gave fluorescent analogs of phosphatidylinositol (PtdIns, 1) and PtdIns(4,5)-bisphosphate (PtdIns(4,5)P₂, 2). Unlike the corresponding phosphoramidate, 3 was stable at -20 °C for several months, making it a useful intermediate for the synthesis of myo-inositol phospholipids.

Original language	English (US)
Pages (from-to)	2921-2924
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(98)00418-3
State	Published - May 7 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)00418-3

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title = "Synthesis of fluorescent phosphatidylinositols using a novel inositol H- phosphonate",

abstract = "Coupling of 1,2-diradyl-sn-glycerol 5 with the novel inositol H- phosphonate derivative, 6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol H-phosphonate (3), gave fluorescent analogs of phosphatidylinositol (PtdIns, 1) and PtdIns(4,5)-bisphosphate (PtdIns(4,5)P2, 2). Unlike the corresponding phosphoramidate, 3 was stable at -20 °C for several months, making it a useful intermediate for the synthesis of myo-inositol phospholipids.",

author = "Leung, \{Lawrence W.\} and Catherine Vilch{\`e}ze and Robert Bittman",

note = "Funding Information: We thank the Michigan State University Mass Spectrometry Facility for recording the mass spectra the National Science Foundation (Grant CHE-9408535) for funds for purchase ofa 400-MHz NMR spectrometer. References and Notes",

year = "1998",

month = may,

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doi = "10.1016/S0040-4039(98)00418-3",

language = "English (US)",

volume = "39",

pages = "2921--2924",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "19",

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TY - JOUR

T1 - Synthesis of fluorescent phosphatidylinositols using a novel inositol H- phosphonate

AU - Leung, Lawrence W.

AU - Vilchèze, Catherine

AU - Bittman, Robert

N1 - Funding Information: We thank the Michigan State University Mass Spectrometry Facility for recording the mass spectra the National Science Foundation (Grant CHE-9408535) for funds for purchase ofa 400-MHz NMR spectrometer. References and Notes

PY - 1998/5/7

Y1 - 1998/5/7

N2 - Coupling of 1,2-diradyl-sn-glycerol 5 with the novel inositol H- phosphonate derivative, 6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol H-phosphonate (3), gave fluorescent analogs of phosphatidylinositol (PtdIns, 1) and PtdIns(4,5)-bisphosphate (PtdIns(4,5)P2, 2). Unlike the corresponding phosphoramidate, 3 was stable at -20 °C for several months, making it a useful intermediate for the synthesis of myo-inositol phospholipids.

AB - Coupling of 1,2-diradyl-sn-glycerol 5 with the novel inositol H- phosphonate derivative, 6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol H-phosphonate (3), gave fluorescent analogs of phosphatidylinositol (PtdIns, 1) and PtdIns(4,5)-bisphosphate (PtdIns(4,5)P2, 2). Unlike the corresponding phosphoramidate, 3 was stable at -20 °C for several months, making it a useful intermediate for the synthesis of myo-inositol phospholipids.

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U2 - 10.1016/S0040-4039(98)00418-3

DO - 10.1016/S0040-4039(98)00418-3

M3 - Article

AN - SCOPUS:0032492945

SN - 0040-4039

VL - 39

SP - 2921

EP - 2924

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Synthesis of fluorescent phosphatidylinositols using a novel inositol H- phosphonate

Abstract

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