Absolute Configurations and Stability of Cyclic Guanosine Mono-adducts with Glyoxal and Methylglyoxal

doi:10.1002/chir.20875

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	Absolute Configurations and Stability of Cyclic Guanosine Mono-adducts with Glyoxal and Methylglyoxal
	Lai, Congfang; Lin, Guangxin; Wang, Wenyue; Luo, Hai
刊名	CHIRALITY
	2011-08-01
卷号	23 期号:7 页码:487-494
关键词	Glyoxal/methylglyoxal Guanosine Adduct Circular Dichroism Octant Rule Diastereoisomer Racemization
ISSN号	0899-0042
DOI	10.1002/chir.20875
英文摘要	Glyoxal and methylglyoxal are two endogenous and mutagenic 1,2-dicarbonyl compounds, which can readily form adducts with guanosine. The molecular structures of cyclic guanosine-glyoxal (G-g) and guanosine-methylglyoxal (G-mg) mono-adducts have been extensively studied before. However, diastereoisomers of these adducts have not yet been studied in detail. In this work, one pair of G-g and two pairs of G-mg diastereoisomers were baseline separated by reverse phase HPLC, whose structures were identified as the previously reported cyclic forms, and their absolute configurations were determined by circular dichroism, the octant rule, and molecular modeling. According to the HPLC elution order, configurations of two G-g (as well as trans G-mg) were (6R,7R) and (6S,7S), respectively. Meanwhile, the stability of each isomer in neutral solution was also investigated, which revealed the stability order G-g > cis G-mg > trans G-mg and also indicated distinct transformation processes for different G-mg configurations. Trans G-mg only racemized between each other, while cis G-mg transformed to both cis and trans forms. Different intermediates in the racemization processes were proposed to explain the observations. These results may shed light on further understanding the roles of these two small molecules in mutagenesis. Chirality 23: 487-494, 2011. (C) 2011 Wiley-Liss, Inc.
语种	英语
出版者	WILEY-BLACKWELL
WOS记录号	WOS:000293012700001
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/73167]
专题	中国科学院化学研究所
通讯作者	Luo, Hai
作者单位	Peking Univ, Beijing Natl Lab Mol Sci, Coll Chem & Mol Engn, Beijing 100871, Peoples R China
推荐引用方式 GB/T 7714	Lai, Congfang,Lin, Guangxin,Wang, Wenyue,et al. Absolute Configurations and Stability of Cyclic Guanosine Mono-adducts with Glyoxal and Methylglyoxal[J]. CHIRALITY,2011,23(7):487-494.
APA	Lai, Congfang,Lin, Guangxin,Wang, Wenyue,&Luo, Hai.(2011).Absolute Configurations and Stability of Cyclic Guanosine Mono-adducts with Glyoxal and Methylglyoxal.CHIRALITY,23(7),487-494.
MLA	Lai, Congfang,et al."Absolute Configurations and Stability of Cyclic Guanosine Mono-adducts with Glyoxal and Methylglyoxal".CHIRALITY 23.7(2011):487-494.