Design and synthesis of an inositol phosphate analog based on computational docking studies

Zhenghong Peng; David Maxwell; Duoli Sun; Yunming Ying; Paul T. Schuber; Basvoju A. Bhanu Prasad; Juri Gelovani; Wai Kwan Alfred Yung; William G. Bornmann

doi:10.1016/j.tet.2013.11.092

Design and synthesis of an inositol phosphate analog based on computational docking studies

Zhenghong Peng
, David Maxwell
, Duoli Sun
, Yunming Ying
, Paul T. Schuber
, Basvoju A. Bhanu Prasad
, Juri Gelovani
, Wai Kwan Alfred Yung
, William G. Bornmann

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

5 Scopus citations

Abstract

A virtual library of 54 inositol analog mimics of In(1,4,5)P₃ has been docked, scored, and ranked within the binding site of human inositol 1,4,5-trisphosphate 3-kinase A (IP₃-3KA). Chemical synthesis of the best scoring structure that also met distance criteria for 3′-OH to-P in phosphate has been attempted along with the synthesis of (1S,2R,3S,4S)-3-fluoro- 2,4-dihydroxycyclohexanecarboxylic acid as an inositol analog, useful for non-invasive visualization and quantitation of IP₃-3KA enzymatic activity.

Original language	English (US)
Pages (from-to)	984-990
Number of pages	7
Journal	Tetrahedron
Volume	70
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2013.11.092
State	Published - Jan 28 2014

Keywords

(+)-Cyclophellitol
F-FDMCI- 3′-phosphate
IP-3K
Inositol
Ins(1,4,5)P

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.11.092

Cite this

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title = "Design and synthesis of an inositol phosphate analog based on computational docking studies",

abstract = "A virtual library of 54 inositol analog mimics of In(1,4,5)P3 has been docked, scored, and ranked within the binding site of human inositol 1,4,5-trisphosphate 3-kinase A (IP3-3KA). Chemical synthesis of the best scoring structure that also met distance criteria for 3′-OH to-P in phosphate has been attempted along with the synthesis of (1S,2R,3S,4S)-3-fluoro- 2,4-dihydroxycyclohexanecarboxylic acid as an inositol analog, useful for non-invasive visualization and quantitation of IP3-3KA enzymatic activity.",

keywords = "(+)-Cyclophellitol, F-FDMCI- 3′-phosphate, IP-3K, Inositol, Ins(1,4,5)P",

author = "Zhenghong Peng and David Maxwell and Duoli Sun and Yunming Ying and Schuber, \{Paul T.\} and \{Bhanu Prasad\}, \{Basvoju A.\} and Juri Gelovani and \{Alfred Yung\}, \{Wai Kwan\} and Bornmann, \{William G.\}",

year = "2014",

month = jan,

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doi = "10.1016/j.tet.2013.11.092",

language = "English (US)",

volume = "70",

pages = "984--990",

journal = "Tetrahedron",

issn = "0040-4020",

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TY - JOUR

T1 - Design and synthesis of an inositol phosphate analog based on computational docking studies

AU - Peng, Zhenghong

AU - Maxwell, David

AU - Sun, Duoli

AU - Ying, Yunming

AU - Schuber, Paul T.

AU - Bhanu Prasad, Basvoju A.

AU - Gelovani, Juri

AU - Alfred Yung, Wai Kwan

AU - Bornmann, William G.

PY - 2014/1/28

Y1 - 2014/1/28

N2 - A virtual library of 54 inositol analog mimics of In(1,4,5)P3 has been docked, scored, and ranked within the binding site of human inositol 1,4,5-trisphosphate 3-kinase A (IP3-3KA). Chemical synthesis of the best scoring structure that also met distance criteria for 3′-OH to-P in phosphate has been attempted along with the synthesis of (1S,2R,3S,4S)-3-fluoro- 2,4-dihydroxycyclohexanecarboxylic acid as an inositol analog, useful for non-invasive visualization and quantitation of IP3-3KA enzymatic activity.

AB - A virtual library of 54 inositol analog mimics of In(1,4,5)P3 has been docked, scored, and ranked within the binding site of human inositol 1,4,5-trisphosphate 3-kinase A (IP3-3KA). Chemical synthesis of the best scoring structure that also met distance criteria for 3′-OH to-P in phosphate has been attempted along with the synthesis of (1S,2R,3S,4S)-3-fluoro- 2,4-dihydroxycyclohexanecarboxylic acid as an inositol analog, useful for non-invasive visualization and quantitation of IP3-3KA enzymatic activity.

KW - (+)-Cyclophellitol

KW - F-FDMCI- 3′-phosphate

KW - IP-3K

KW - Inositol

KW - Ins(1,4,5)P

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UR - https://www.scopus.com/pages/publications/84891828747#tab=citedBy

U2 - 10.1016/j.tet.2013.11.092

DO - 10.1016/j.tet.2013.11.092

M3 - Article

C2 - 25110363

AN - SCOPUS:84891828747

SN - 0040-4020

VL - 70

SP - 984

EP - 990

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

Design and synthesis of an inositol phosphate analog based on computational docking studies

Abstract

Keywords

ASJC Scopus subject areas

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