Skip to main content
SpringerLink
Log in

Synthesis and applications of phosphatidylinositols and their analogues

  • Carbohydrates and Lipids: Synthesis and Outlook
  • Published:
Proceedings of the Indian Academy of Sciences - Chemical Sciences Aims and scope Submit manuscript

Abstract

There is an upsurge of interest in the chemistry and biochemistry of phosphoinotides, their analogues and the related enzymes due to their involvement in the inositol phosphates mediated cellular signal transduction pathways. The present review deals with the recent developments in the synthesis and applications of phosphatidylinositol and its derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

Ptdlns:

phosphatidylinositol

AMP:

adinosinemonophosphate

PtdIns(3)P:

phosphatidylinositol-3-phosphate

Ptdlns (4) P:

phosphatidylinositol-4-phosphate

Ptdlns (3,4) P2 :

phosphatidylinositol-3,4-bisphosphate

PtdIns(4,5)P2 :

phosphatidylinositol-4,5-bisphosphate

PtdIns(3,4,5)P3 :

phosphatidy-linositol-3,4,5-triphosphate

Ins(l)P:

Myo-inositol-1 -phosphate

Ins(l,2-cyc)P:

Myo-inositol-l,2-cyclic-phosphate

Ins(l,4,5) P3 :

Myo-inositol-l,4,5-triphosphate

DAG:

diacylglycerol

TBDMS:

t-butyldimethyl-silyl

MSNT:

1-(mesitylene-2-sulphonyl)-3-nitro-l,2,4-triazole

NPCL:

5,5-dimethyl-2-oxo-2-chloro-l,3,2-dioxaphophorinan

PLA2:

phospholipase A2

PLD:

phospholipase D

PI-PLC:

phosphatidylinositol-specific phospholipase C

PI-4-kinase:

phosphatidylinositol-4-kinase

P:

PO3H2

Bn:

benzyl

Pro:

propenyl

DAG:

diacylglycerol

A:

allyl

MOM:

methoxymethyl

Ac:

acetyl

THP:

tetrahydropyranyl

PMB:

p-methoxybenzyl

nD:

D-enantiomer of the compoundn

nL:

L-enantiomer of the compoundn

nHL:

racematen)

References

  • Alisi M A, Brufani M, Filocamo L, Gostoli G, Cellai L, Ianell, M A, Melino G, Cesta M C and Lappa S 1993Bioorg. Med. Chem. Lett. 3 1931

    Article  CAS  Google Scholar 

  • Alisi M A, Brufani M, Filocamo L, Gostoli G, Lappa S, Maiorana S, Cesta M C, Ferrari E and Pagella P 1992aTetrahedron Lett. 33 3891

    Article  CAS  Google Scholar 

  • Alisi M A, Brufani M, Filocamo L, Gostoli G, Maiorana S, Cesta M C, Ferrari E, Lappa S and Pagella P 1992bTetrahedron Lett. 33 7793

    Article  CAS  Google Scholar 

  • Anderson R J, Lothrop W C and Creighton M M 1938J. Biol. Chem. 125 299

    CAS  Google Scholar 

  • Anderson R J and Roberto E G 1930J. Am. Chem. Soc. 52 5023

    Article  CAS  Google Scholar 

  • Billington D C 1989Chem. Soc. Rev. 18 83

    Article  CAS  Google Scholar 

  • Bruzik K S, Morocho A M, Jhon D Y, Rhee S G and Tsai M D 1992Biochemistry 29 2747

    Google Scholar 

  • Bruzik K S and Tsai M D 1992J. Am. Chem. Soc. 114 6361

    Article  CAS  Google Scholar 

  • Bugaut M, Kuksis A and Myher J J 1985Biochim. Biophys. Acta. 835 304

    CAS  Google Scholar 

  • Chan B L, Chao M V and Saltiel A R 1989Proc. Natl. Acad. Sci. USA 86 1756

    Article  CAS  Google Scholar 

  • Cleves A, McGee T and Bankaitis V 1991Trends Cell Biol. 1 30

    Article  CAS  Google Scholar 

  • Cosgrove D J 1980Inositol phosphates. Their chemistry, biochemistry and physiology (New York: Else vier)

    Google Scholar 

  • Cottaz S, Brimacombe J S and Ferguson M A J 1993J. Chem. Soc., Perkin Trans. 1 2945

    Article  Google Scholar 

  • Dawson R M C, Freinkel N, Jungalwala F B and Clarke N 1971Biochem J. 122 605

    CAS  Google Scholar 

  • Dreef C E, Douwes M, Elie C J J, van der Marel G A and van Boom J H 1991Synthesis 443

  • Dreef C E, Elie C J J, Hoogerhout P, van der Marel G A and van Boom J H 1988Tetrahedron Lett. 29 6513

    Article  CAS  Google Scholar 

  • Elie C J J, Dreef C E, Verduyn R, van der Marel G A and van Boom J H 1989Tetrahedron 45 3477

    Article  CAS  Google Scholar 

  • Elie C J J, Verduyn R, Dreef C E, van der Marel G A and van Boom J H 1992J. Carbohyd. Chem. 11 715

    Article  CAS  Google Scholar 

  • Ferguson M A J, Low M G and Cross G A M 1985J. Biol. Chem. 260 14547

    CAS  Google Scholar 

  • Ferguson M A J and Williams A F 1988Annu. Rev. Biochem. 57 285

    Article  CAS  Google Scholar 

  • Filtuh E and Eibl H 1992Chem. Phys. Lipids 60 253

    Article  Google Scholar 

  • Folch J and Wooley D W 1942J. Biol. Chem. 142 963

    CAS  Google Scholar 

  • Frantova A Y, Stepanov A E, Bushnev A S, Zvonkova E N and Shvets VI 1992Tetrahedron Lett. 33 3539

    Article  CAS  Google Scholar 

  • Gadella T W A Jr, Moritz A, Westerman J and Wirtz K W A 1990Biochemistry 29 3389

    Article  CAS  Google Scholar 

  • Garigapati R and Roberts M F 1993Tetrahedron Lett. 34(a) 769, (b) 5579

    Article  Google Scholar 

  • Hay J C and Majrtin T F J 1993Nature (London) 366 572

    Article  CAS  Google Scholar 

  • Hendrickson H S, Hendrickson E K, Johnson J L, Khan T H and Chial H J 1992Biochemistry 12169

  • Hendrickson E K, Johnson J L and Hendrickson H S 1991Bioorg. Med. Chem. Lett. (a) 615, (b) 619

    Google Scholar 

  • James D, Massy R and Wyss P 1990Helv. Chim. Acta. 73 1037

    Article  Google Scholar 

  • Kaufman F, Massy D J R, Pirson W and Wyss P 1991 inInositol phosphates and derivatives: Synthesis,biochemistry and therapeutic potential (ed.) A B Reitz (ACS Symposium series 463) p. 202

  • Kim J W, Ryu S H and Rhee S G 1989Biochem. Biophys. Res. Commun. 163 177

    Article  CAS  Google Scholar 

  • Koke J A, Yang M, Henner D J, Volwerk J J and Griffith O H 1991Protein Expression Purification 2 51

    Article  CAS  Google Scholar 

  • Kratzer B, Mayer T G and Schmidt R R 1993Tetrahedron Lett. 34 6881

    Article  CAS  Google Scholar 

  • Kuipers O P, Dekker N, Verheij H M and de Haas G H 1990Biochemistry 29 6994

    Article  Google Scholar 

  • Kume T, Taguchi R, Tomita M, Tokuyama S, Morizawa K, Nakachi N, Hirano I and Ikezawa H 1992Chem. Pharm. Bull. 40 2133

    CAS  Google Scholar 

  • Lee Y C and Ballou C E 1965Biochemistry 4 1395

    Article  CAS  Google Scholar 

  • Leigh A J, Volwerk J J, Griffith O H and Keana J F W 1992Biochemistry 31 8978

    Article  CAS  Google Scholar 

  • Lewis K A, Garigapati V R, Zhou C and Roberts M F 1993Biochemistry 32 8836

    Article  CAS  Google Scholar 

  • Lin G, Bennet F C and Tsai M D 1990Biochemistry 29 2747

    Article  CAS  Google Scholar 

  • Lindh I and Stawinski 1989J. Org. Chem. 54 1338, and references cited therein

    Article  CAS  Google Scholar 

  • Majerus P W, Ross T S, Cunningham T W, Caldwell K K, Jefferson A B and Bansal U S 1990Cell 63 459

    Article  CAS  Google Scholar 

  • Murakata C and Ogawa T 1991Tetrahedron Lett. 32 101

    Article  CAS  Google Scholar 

  • Murakata C and Ogawa T1992Carbohyd. Res. 235 95

    Article  CAS  Google Scholar 

  • Parthasarathy R and Eisenberg F Jr 1986Biochem. J. 235 313

    CAS  Google Scholar 

  • Potter B V L 1990 InComprehensive medical chemistry (ed.) C Hansch (New York: Pergamon Press) vol. 3

    Google Scholar 

  • Salamonczyk G M and Bruzik K S 1990Tetrahedron Lett. 31 2015

    Article  CAS  Google Scholar 

  • Seitz S P, Kaltenbach R F III, Vreekamp R H, Calabrese J C and Perella F W 1992Bioorg. Med. Chem. Lett. 2 171

    Article  CAS  Google Scholar 

  • Skinner H B 1993EMBO J. 12 4775

    CAS  Google Scholar 

  • Shashidhar M S, Keana J F W, Volwerk J J and Griffith O H 1990aChem. Phys. Lipids 53 103

    Article  CAS  Google Scholar 

  • Shashidhar M S, Keana J F W, Volwerk J J and Griffith O H 1990bChem. Phys. Lipids 56 159

    Article  CAS  Google Scholar 

  • Shashidhar M S, Volwerk J J, Keana J F W and Griffith O H 1990cBiochim. Biophys. Acta 1042 410

    CAS  Google Scholar 

  • Shashidhar M S, Volwerk J J, Keana J F W and Griffith O H 1991aChem. Phys. Lipids 60 101

    Article  CAS  Google Scholar 

  • Shashidhar M S, Volwerk J J, Keana J F W and Griffith O H 1991bAnal. Biochem. 198 10

    Article  CAS  Google Scholar 

  • Volwerk J J, Shashidhar M S, Kuppe A and Griffith O H 1990Biochenistry 29 8056

    CAS  Google Scholar 

  • Whitman M, Downes C P, Keeler M, Keller T and Cantley L 1988Nature (London)332 644

    Article  CAS  Google Scholar 

  • Young R C, Downes C P, Eggleston D S, Jones M, Macphee C H, Rana K K and Ward J G 1990J. Med. Chem. 33 641

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Division of Organic Chemistry (Synthesis), National Chemical Laboratory, 411008, Pune, India

    M. S. Shashidhar

Authors
  1. M. S. Shashidhar
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

NCL commun, no. 6014

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shashidhar, M.S. Synthesis and applications of phosphatidylinositols and their analogues. Proc. Indian Acad. Sci. (Chem. Sci.) 106, 1231–1251 (1994). https://doi.org/10.1007/BF02841930

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02841930

Keywords

Search

Navigation