General Linker Diversification Approach to Bivalent Ligand Assembly: Generation of an Array of Ligands for the Cation-Independent Mannose 6-Phosphate Receptor

Xiang Fei; Megan E. Zavorka; Guillaume Malik; Christopher M. Connelly; Richard G. MacDonald; David B. Berkowitz

doi:10.1021/acs.orglett.7b01914

General Linker Diversification Approach to Bivalent Ligand Assembly: Generation of an Array of Ligands for the Cation-Independent Mannose 6-Phosphate Receptor

Xiang Fei, Megan E. Zavorka, Guillaume Malik, Christopher M. Connelly, Richard G. MacDonald, David B. Berkowitz

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

5 Scopus citations

Abstract

A generalized strategy is presented for the rapid assembly of a set of bivalent ligands with a variety of linking functionalities from a common monomer. Herein, an array of phosphatase-inert mannose-6-phosphonate-presenting ligands for the cation-independent-mannose 6-phosphate receptor (CI-MPR) is constructed. Receptor binding affinity varies with linking functionality - the simple amide and 1,5-triazole(tetrazole) being preferred over the 1,4-triazole. This approach is expected to find application across chemical biology, particularly in glycoscience, wherein multivalency often governs molecular recognition.

Original language	English (US)
Pages (from-to)	4267-4270
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.7b01914
State	Published - Aug 18 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "General Linker Diversification Approach to Bivalent Ligand Assembly: Generation of an Array of Ligands for the Cation-Independent Mannose 6-Phosphate Receptor",

abstract = "A generalized strategy is presented for the rapid assembly of a set of bivalent ligands with a variety of linking functionalities from a common monomer. Herein, an array of phosphatase-inert mannose-6-phosphonate-presenting ligands for the cation-independent-mannose 6-phosphate receptor (CI-MPR) is constructed. Receptor binding affinity varies with linking functionality - the simple amide and 1,5-triazole(tetrazole) being preferred over the 1,4-triazole. This approach is expected to find application across chemical biology, particularly in glycoscience, wherein multivalency often governs molecular recognition.",

author = "Xiang Fei and Zavorka, {Megan E.} and Guillaume Malik and Connelly, {Christopher M.} and MacDonald, {Richard G.} and Berkowitz, {David B.}",

note = "Funding Information: This work was supported in part by NIH 5R01CA91885 & 5R21CA198292 (R.G.M.) and RR016544 (D.B.B.), by Nebraska Research Initiative funds (D.B.B. and R.G.M.), and by the IR/D program associated with D.B.B.'s appointment at the NSF. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b01914",

language = "English (US)",

volume = "19",

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journal = "Organic Letters",

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T1 - General Linker Diversification Approach to Bivalent Ligand Assembly

T2 - Generation of an Array of Ligands for the Cation-Independent Mannose 6-Phosphate Receptor

AU - Fei, Xiang

AU - Zavorka, Megan E.

AU - Malik, Guillaume

AU - Connelly, Christopher M.

AU - MacDonald, Richard G.

AU - Berkowitz, David B.

N1 - Funding Information: This work was supported in part by NIH 5R01CA91885 & 5R21CA198292 (R.G.M.) and RR016544 (D.B.B.), by Nebraska Research Initiative funds (D.B.B. and R.G.M.), and by the IR/D program associated with D.B.B.'s appointment at the NSF. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/8/18

Y1 - 2017/8/18

N2 - A generalized strategy is presented for the rapid assembly of a set of bivalent ligands with a variety of linking functionalities from a common monomer. Herein, an array of phosphatase-inert mannose-6-phosphonate-presenting ligands for the cation-independent-mannose 6-phosphate receptor (CI-MPR) is constructed. Receptor binding affinity varies with linking functionality - the simple amide and 1,5-triazole(tetrazole) being preferred over the 1,4-triazole. This approach is expected to find application across chemical biology, particularly in glycoscience, wherein multivalency often governs molecular recognition.

AB - A generalized strategy is presented for the rapid assembly of a set of bivalent ligands with a variety of linking functionalities from a common monomer. Herein, an array of phosphatase-inert mannose-6-phosphonate-presenting ligands for the cation-independent-mannose 6-phosphate receptor (CI-MPR) is constructed. Receptor binding affinity varies with linking functionality - the simple amide and 1,5-triazole(tetrazole) being preferred over the 1,4-triazole. This approach is expected to find application across chemical biology, particularly in glycoscience, wherein multivalency often governs molecular recognition.

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General Linker Diversification Approach to Bivalent Ligand Assembly: Generation of an Array of Ligands for the Cation-Independent Mannose 6-Phosphate Receptor

Abstract

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