Selective Formation of Chromogen i from N-Acetyl-D-glucosamine upon Lanthanide Coordination

Xiu Ying Zheng; Jun Bo Peng; M. M.Varuni S. Livera; Yun Luo; Ya Yun Wang; Xiang Jian Kong; La Sheng Long; Zhiping Zheng; Lan Sun Zheng

doi:10.1021/acs.inorgchem.6b02589

Selective Formation of Chromogen i from N-Acetyl-D-glucosamine upon Lanthanide Coordination

Xiu Ying Zheng, Jun Bo Peng, M. M.Varuni S. Livera, Yun Luo, Ya Yun Wang, Xiang Jian Kong, La Sheng Long, Zhiping Zheng, Lan Sun Zheng

Chemistry and Biochemistry

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

17 Scopus citations

Abstract

We report two nonanuclear lanthanide complexes, [Ln₉(μ₄-O)(μ₃-OH)₈(LH)₄(OAc)₄(H₂O)₁₂]·5ClO₄·24H₂O (Ln = Gd, 1; Dy, 2), where LH^2- is the doubly deprotonated chiral ligand Chromogen I (2-acetamido-2,3-dideoxy-D-erythro-hex-2-enofuranose), one of the many products from the dehydration of N-acetyl-D-glucosamine (GlcNAc). Mass spectroscopic studies established the solution stability of these clusters. Through hydrogen bonding, the cluster complex self-organizes into a nanostructured 54-metal cagelike assembly featuring six of its units occupying the vertices of an octahedron. Free Chromogen I can be obtained in pure form and high yield by a straightforward workup of the cluster complex. This is the first report of dehydrating GlcNAc without the need of a catalyst or forcing conditions.

Original language	English (US)
Pages (from-to)	110-113
Number of pages	4
Journal	Inorganic Chemistry
Volume	56
Issue number	1
DOIs	https://doi.org/10.1021/acs.inorgchem.6b02589
State	Published - Jan 3 2017

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry

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10.1021/acs.inorgchem.6b02589

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@article{37630c44381e4102a4fbd9bf3af013e0,

title = "Selective Formation of Chromogen i from N-Acetyl-D-glucosamine upon Lanthanide Coordination",

abstract = "We report two nonanuclear lanthanide complexes, [Ln9(μ4-O)(μ3-OH)8(LH)4(OAc)4(H2O)12]·5ClO4·24H2O (Ln = Gd, 1; Dy, 2), where LH2- is the doubly deprotonated chiral ligand Chromogen I (2-acetamido-2,3-dideoxy-D-erythro-hex-2-enofuranose), one of the many products from the dehydration of N-acetyl-D-glucosamine (GlcNAc). Mass spectroscopic studies established the solution stability of these clusters. Through hydrogen bonding, the cluster complex self-organizes into a nanostructured 54-metal cagelike assembly featuring six of its units occupying the vertices of an octahedron. Free Chromogen I can be obtained in pure form and high yield by a straightforward workup of the cluster complex. This is the first report of dehydrating GlcNAc without the need of a catalyst or forcing conditions.",

author = "Zheng, {Xiu Ying} and Peng, {Jun Bo} and Livera, {M. M.Varuni S.} and Yun Luo and Wang, {Ya Yun} and Kong, {Xiang Jian} and Long, {La Sheng} and Zhiping Zheng and Zheng, {Lan Sun}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2017",

month = jan,

day = "3",

doi = "10.1021/acs.inorgchem.6b02589",

language = "English (US)",

volume = "56",

pages = "110--113",

journal = "Inorganic Chemistry",

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publisher = "American Chemical Society",

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T1 - Selective Formation of Chromogen i from N-Acetyl-D-glucosamine upon Lanthanide Coordination

AU - Zheng, Xiu Ying

AU - Peng, Jun Bo

AU - Livera, M. M.Varuni S.

AU - Luo, Yun

AU - Wang, Ya Yun

AU - Kong, Xiang Jian

AU - Long, La Sheng

AU - Zheng, Zhiping

AU - Zheng, Lan Sun

PY - 2017/1/3

Y1 - 2017/1/3

N2 - We report two nonanuclear lanthanide complexes, [Ln9(μ4-O)(μ3-OH)8(LH)4(OAc)4(H2O)12]·5ClO4·24H2O (Ln = Gd, 1; Dy, 2), where LH2- is the doubly deprotonated chiral ligand Chromogen I (2-acetamido-2,3-dideoxy-D-erythro-hex-2-enofuranose), one of the many products from the dehydration of N-acetyl-D-glucosamine (GlcNAc). Mass spectroscopic studies established the solution stability of these clusters. Through hydrogen bonding, the cluster complex self-organizes into a nanostructured 54-metal cagelike assembly featuring six of its units occupying the vertices of an octahedron. Free Chromogen I can be obtained in pure form and high yield by a straightforward workup of the cluster complex. This is the first report of dehydrating GlcNAc without the need of a catalyst or forcing conditions.

AB - We report two nonanuclear lanthanide complexes, [Ln9(μ4-O)(μ3-OH)8(LH)4(OAc)4(H2O)12]·5ClO4·24H2O (Ln = Gd, 1; Dy, 2), where LH2- is the doubly deprotonated chiral ligand Chromogen I (2-acetamido-2,3-dideoxy-D-erythro-hex-2-enofuranose), one of the many products from the dehydration of N-acetyl-D-glucosamine (GlcNAc). Mass spectroscopic studies established the solution stability of these clusters. Through hydrogen bonding, the cluster complex self-organizes into a nanostructured 54-metal cagelike assembly featuring six of its units occupying the vertices of an octahedron. Free Chromogen I can be obtained in pure form and high yield by a straightforward workup of the cluster complex. This is the first report of dehydrating GlcNAc without the need of a catalyst or forcing conditions.

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DO - 10.1021/acs.inorgchem.6b02589

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VL - 56

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JO - Inorganic Chemistry

JF - Inorganic Chemistry

IS - 1

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Selective Formation of Chromogen i from N-Acetyl-D-glucosamine upon Lanthanide Coordination

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CCDC 1502883: Experimental Crystal Structure Determination

CCDC 1502882: Experimental Crystal Structure Determination

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Selective Formation of Chromogen i from N-Acetyl-D-glucosamine upon Lanthanide Coordination

Abstract

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CCDC 1502883: Experimental Crystal Structure Determination

CCDC 1502882: Experimental Crystal Structure Determination

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