Synthesis of bi- and tricyclic analogues of myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate with extended carbon backbone

Andrew Schnaars; Carsten Schultz

doi:10.1016/S0040-4020(00)01021-8

Synthesis of bi- and tricyclic analogues of myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate with extended carbon backbone

Andrew Schnaars, Carsten Schultz

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

11 Scopus citations

Abstract

myo-Inositol 3,4,5,6-tetrakisphosphate [Ins(3,4,5,6)P₄] and its enantiomer exhibit distinct functions in the regulation of transepithelial chloride secretion. In search for agonists and antagonists of these potential messengers we synthesized a bicyclic oxepin analogue and a tricyclic analogue with a selfprotecting dioxolane moiety. The carbon backbone extension was linked to the C2 position. Ring closure was achieved by a metathesis reaction.

Original language	English (US)
Pages (from-to)	519-524
Number of pages	6
Journal	Tetrahedron
Volume	57
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4020(00)01021-8
State	Published - Jan 14 2001
Externally published	Yes

Keywords

Cyclitols
Inositol phosphates
Ring-closure metathesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4020(00)01021-8

Cite this

@article{18052eee3d1445e2aeebf61d258a1c93,

title = "Synthesis of bi- and tricyclic analogues of myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate with extended carbon backbone",

abstract = "myo-Inositol 3,4,5,6-tetrakisphosphate [Ins(3,4,5,6)P4] and its enantiomer exhibit distinct functions in the regulation of transepithelial chloride secretion. In search for agonists and antagonists of these potential messengers we synthesized a bicyclic oxepin analogue and a tricyclic analogue with a selfprotecting dioxolane moiety. The carbon backbone extension was linked to the C2 position. Ring closure was achieved by a metathesis reaction.",

keywords = "Cyclitols, Inositol phosphates, Ring-closure metathesis",

author = "Andrew Schnaars and Carsten Schultz",

note = "Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft (Schu 943/1-7) and the Fonds der Chemischen Industrie. ",

year = "2001",

month = jan,

day = "14",

doi = "10.1016/S0040-4020(00)01021-8",

language = "English (US)",

volume = "57",

pages = "519--524",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "3",

}

TY - JOUR

T1 - Synthesis of bi- and tricyclic analogues of myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate with extended carbon backbone

AU - Schnaars, Andrew

AU - Schultz, Carsten

N1 - Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft (Schu 943/1-7) and the Fonds der Chemischen Industrie.

PY - 2001/1/14

Y1 - 2001/1/14

N2 - myo-Inositol 3,4,5,6-tetrakisphosphate [Ins(3,4,5,6)P4] and its enantiomer exhibit distinct functions in the regulation of transepithelial chloride secretion. In search for agonists and antagonists of these potential messengers we synthesized a bicyclic oxepin analogue and a tricyclic analogue with a selfprotecting dioxolane moiety. The carbon backbone extension was linked to the C2 position. Ring closure was achieved by a metathesis reaction.

AB - myo-Inositol 3,4,5,6-tetrakisphosphate [Ins(3,4,5,6)P4] and its enantiomer exhibit distinct functions in the regulation of transepithelial chloride secretion. In search for agonists and antagonists of these potential messengers we synthesized a bicyclic oxepin analogue and a tricyclic analogue with a selfprotecting dioxolane moiety. The carbon backbone extension was linked to the C2 position. Ring closure was achieved by a metathesis reaction.

KW - Cyclitols

KW - Inositol phosphates

KW - Ring-closure metathesis

UR - http://www.scopus.com/inward/record.url?scp=0035857258&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035857258&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(00)01021-8

DO - 10.1016/S0040-4020(00)01021-8

M3 - Article

AN - SCOPUS:0035857258

SN - 0040-4020

VL - 57

SP - 519

EP - 524

JO - Tetrahedron

JF - Tetrahedron

IS - 3

ER -

Synthesis of bi- and tricyclic analogues of myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate with extended carbon backbone

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this