Design of α-Selective Glycopyranosyl Donors Relying on Remote Anchimeric Assistance

Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]
Bozhena S KomarovaNikolay E Nifantiev

Abstract

Oligosaccharides have a variety of versatile biological effects, but unlike peptides and oligonucleotides, investigation of the roles of oligosaccharides is not easy. Since biosynthesis of oligosaccharides does not comply with direct genetic control, their isolation from natural sources and biotechnological preparation are complicated, due to the heterogeneous composition of raw carbohydrates. Oligosaccharide synthesis is needed for the establishment or confirmation of the structure of natural glycocompounds. Also, synthetically prepared, defined oligosaccharides and their derivatives are becoming increasingly important tools for many biological and immunological research projects. The key step of oligosaccharide synthesis involves glycosylation, a reaction that builds glycosidic bonds. Usually, construction of 1,2-trans-bonds is easy, and therefore, this reaction can even be included into automated syntheses. At this time, installation of the 1,2-cis-bond remains simultaneously frustrating and compelling. In our and other laboratories, a strategy of α-selective (1,2-cis) glycosylation, relying on remote anchimeric assistance with acyl groups, is studied. The state of the art in this work is summarized in this review.

References

Sep 27, 2001·Journal of the American Chemical Society·O J PlanteP H Seeberger
Jul 5, 2003·Organic Letters·Yoshihiro NishidaKazukiyo Kobayashi
Aug 14, 2003·Chemistry : a European Journal·Mads H Clausen, Robert Madsen
Aug 25, 2005·Journal of the American Chemical Society·Jin-Hwan KimGeert-Jan Boons
Jul 5, 2007·The Journal of Organic Chemistry·Silvia ValerioAlessandra Ravidà
Apr 29, 2008·Carbohydrate Research·Archana R ParameswarAlexei V Demchenko
Oct 10, 2008·The Journal of Organic Chemistry·Bozhena S KomarovaNikolay E Nifantiev
Jun 1, 2010·Carbohydrate Research·Chengli ZongYingxia Li
Dec 7, 2010·Chemistry : a European Journal·Mads HeuckendorffMikael Bols
Dec 17, 2010·Organic Letters·Thomas J BoltjeGeert-Jan Boons
Feb 15, 2011·Carbohydrate Research·Vadim B KrylovNikolay E Nifantiev
May 14, 2011·Organic Letters·Laurel K MydockAlexei V Demchenko
Dec 6, 2011·The Journal of Organic Chemistry·Sophon KaeothipAlexei V Demchenko
Aug 1, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Akihiko KoizumiNoriyasu Hada
Nov 22, 2012·Journal of the American Chemical Society·Jagodige P Yasomanee, Alexei V Demchenko
Jan 3, 2014·Organic & Biomolecular Chemistry·Shaheen K MulaniKwok-Kong Tony Mong
Jun 25, 2014·Carbohydrate Research·Darshita Budhadev, Balaram Mukhopadhyay
Dec 4, 2014·Chemical Communications : Chem Comm·Jyh-Herng RueiKwok-Kong Tony Mong
Nov 5, 2015·Organic & Biomolecular Chemistry·Dmitry Z VinnitskiyNikolay E Nifantiev

❮ Previous
Next ❯

Citations

Mar 24, 2016·Journal of the American Chemical Society·Someswara Rao Sanapala, Suvarn S Kulkarni
May 26, 2016·The Journal of Organic Chemistry·Mads HeuckendorffHenrik H Jensen
Jul 19, 2018·Chemistry, an Asian Journal·Sloane O'NeillMaciej A Walczak
Aug 14, 2020·Organic & Biomolecular Chemistry·Qingpeng ZhaoJian Gao
Aug 20, 2020·Organic & Biomolecular Chemistry·Catherine AlexAlexei V Demchenko
Aug 14, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Evgeny V PospelovAlexey Yu Sukhorukov
Mar 10, 2021·Organic & Biomolecular Chemistry·Catherine AlexAlexei V Demchenko
Mar 31, 2021·The Journal of Organic Chemistry·Dennis P A WanderJeroen D C Codée
Mar 30, 2021·Russian Journal of Bioorganic Chemistry·M L GeningN E Nifantiev
Mar 30, 2021·Russian Journal of Bioorganic Chemistry·E A Khatuntseva, N E Nifantiev
Jun 12, 2021·Journal of the American Chemical Society·Yuntao ZhuPeter H Seeberger
Aug 14, 2021·Beilstein Journal of Organic Chemistry·Giulio FittolaniMartina Delbianco
Jun 6, 2018·Chemical Reviews·Suvarn S KulkarniShang-Cheng Hung
Mar 20, 2018·Journal of the American Chemical Society·Liming WangJeroen D C Codée
Oct 17, 2020·The Journal of Organic Chemistry·Melanie ShadrickAlexei V Demchenko
Feb 5, 2019·Journal of the American Chemical Society·Larissa Krasnova, Chi-Huey Wong
Jan 9, 2020·Journal of the American Chemical Society·Ekaterina D KazakovaNikolay E Nifantiev
Dec 21, 2021·The Journal of Organic Chemistry·Catherine Alex, Alexei V Demchenko

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.