Syntheses and biological activities of deoxy-d-allose fatty acid ester analogs

Bioscience, Biotechnology, and Biochemistry
Md Tazul Islam ChowdhuryYasuhiro Kawanami

Abstract

We describe the syntheses of three different deoxy-D-allose analogs [2-deoxy-d-allose (2-DOAll), 1,2-dideoxy-d-allose (1,2-DOAll), and 1,2-didehydro-1,2-dideoxy-d-allose (1,2-DHAll)] and their fatty acid esters via regioselective lipase-catalyzed transesterification. Among them, 2-DOAll and its decanoate (2-DOAll-C10) showed higher inhibitory activity on plant growth, which is similar to d-allose (All) [corrected] and its decanoate (All-C10). Bioassay results of deoxy-All-C10 on four plant species suggest that the hydroxy group at the C-1 position might be important showing growth inhibitory activity. In addition, co-addition of gibberellin (GA3) with 1,2-DHAll-C10 and 2-DOAll-C10 recovered plant growth, suggesting that they might mainly inhibit biosynthesis of gibberellin.

References

Nov 1, 1995·The American Journal of Clinical Nutrition·G V LevinJ R Beadle
Jun 6, 2002·Die Naturwissenschaften·Ken Izumori
Nov 8, 2003·Journal of Hepato-biliary-pancreatic Surgery·Mohammad Akram HossainHajime Maeta
Mar 12, 2004·Annual Review of Plant Physiology and Plant Molecular Biology·Wilhelm Rademacher
Apr 26, 2005·Bioscience, Biotechnology, and Biochemistry·Ghanwa AfachKen Izumori
Oct 20, 2005·Journal of Bioscience and Bioengineering·Akiko MurataMasaaki Tokuda
May 24, 2006·Journal of Biotechnology·Ken Izumori
Aug 24, 2006·Bioscience, Biotechnology, and Biochemistry·Ghanwa AfachKen Izumori
Jan 12, 2007·Applied Microbiology and Biotechnology·Tom Birger GranströmMatti Leisola
Jul 25, 2007·Cryobiology·Li SuiMasaaki Tokuda
Oct 22, 2008·Journal of Bioscience and Bioengineering·Fuminori YamaguchiMasaaki Tokuda
Dec 9, 2008·Organic Letters·William J Morris, Matthew D Shair
Jan 9, 2010·Bioscience, Biotechnology, and Biochemistry·Miyuki KobayashiYasuhiro Kawanami
Mar 29, 2011·Cancer Letters·Hiroshi HoshikawaNozomu Mori
Sep 6, 2011·Journal of Bioscience and Bioengineering·Yasuhiro IshiharaKouichi Itoh
May 10, 2012·Applied Microbiology and Biotechnology·Wanmeng MuLeon Zhou

❮ Previous
Next ❯

Citations

Mar 8, 2018·Bioscience, Biotechnology, and Biochemistry·Md Tazul Islam ChowdhuryYasuhiro Kawanami
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nikola MijailovicAziz Aziz

❮ Previous
Next ❯

Methods Mentioned

BETA
column chromatography

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.

Related Papers

Advances in Prostaglandin and Thromboxane Research
S OhuchidaM Hayashi
Bioscience, Biotechnology, and Biochemistry
Miyuki KobayashiYasuhiro Kawanami
© 2021 Meta ULC. All rights reserved