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异鸟苷磷酸酰胺的合成,甘油核酸的一种异构体。

Synthesis of phosphoramidites of isoGNA, an isomer of glycerol nucleic acid.

机构信息

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Rd, La Jolla, CA 92037, USA.

出版信息

Beilstein J Org Chem. 2014 Sep 8;10:2131-8. doi: 10.3762/bjoc.10.220. eCollection 2014.

DOI:10.3762/bjoc.10.220
PMID:25246971
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4168771/
Abstract

IsoGNA, an isomer of glycerol nucleic acid GNA, is a flexible (acyclic) nucleic acid with bases directly attached to its linear backbone. IsoGNA exhibits (limited) base-pairing properties which are unique compared to other known flexible nucleic acids. Herein, we report on the details of the preparation of isoGNA phosphoramidites and an alternative route for the synthesis of the adenine derivative. The synthetic improvements described here enable an easy access to isoGNA and allows for the further exploration of this structural unit in oligonucleotide chemistry thereby spurring investigations of its usefulness and applicability.

摘要

IsoGNA(甘油核酸 GNA 的异构体)是一种具有碱基直接连接到其线性主链上的灵活(无环)核酸。与其他已知的灵活核酸相比,IsoGNA 表现出(有限的)碱基配对特性。在此,我们报告了 IsoGNA 亚磷酰胺的制备细节和腺嘌呤衍生物合成的替代途径。此处描述的合成改进使 IsoGNA 易于获得,并允许进一步探索该结构单元在寡核苷酸化学中的应用,从而促进对其有用性和适用性的研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/19efa1a749a9/Beilstein_J_Org_Chem-10-2131-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/3061fb4470bf/Beilstein_J_Org_Chem-10-2131-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/a52fbd3bbc74/Beilstein_J_Org_Chem-10-2131-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/7b21401acbf7/Beilstein_J_Org_Chem-10-2131-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/383abbfad945/Beilstein_J_Org_Chem-10-2131-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/b6101a2a1dbc/Beilstein_J_Org_Chem-10-2131-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/b9f05c9dd675/Beilstein_J_Org_Chem-10-2131-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/c4d707d8b19c/Beilstein_J_Org_Chem-10-2131-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/19efa1a749a9/Beilstein_J_Org_Chem-10-2131-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/3061fb4470bf/Beilstein_J_Org_Chem-10-2131-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/a52fbd3bbc74/Beilstein_J_Org_Chem-10-2131-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/7b21401acbf7/Beilstein_J_Org_Chem-10-2131-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/383abbfad945/Beilstein_J_Org_Chem-10-2131-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/b6101a2a1dbc/Beilstein_J_Org_Chem-10-2131-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/b9f05c9dd675/Beilstein_J_Org_Chem-10-2131-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/c4d707d8b19c/Beilstein_J_Org_Chem-10-2131-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d56/4168771/19efa1a749a9/Beilstein_J_Org_Chem-10-2131-g009.jpg

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