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Beta-d-Fructofuranose

A furanose is a collective term for carbohydrates that have a chemical structure that includes a five-membered ring system consisting of four carbon atoms and one oxygen atom. The name derives from its similarity to the oxygen heterocycle furan, but the furanose ring does not have double bonds. ^[1]

Structural properties

The chemical structure of ribose in its furanose form. The wavy bond indicates a mixture of β-ribofuranose and α-ribofuranose.

The furanose ring is a cyclic hemiacetal of an aldopentose or a cyclic hemiketal of a ketohexose.

A furanose ring structure consists of four carbon and one oxygen atom with the anomeric carbon to the right of the oxygen. The highest numbered chiral carbon (typically to the left of the oxygen in a Haworth projection) determines whether or not the structure has a d-configuration or L-configuration. In an l-configuration furanose, the substituent on the highest numbered chiral carbon is pointed downwards out of the plane, and in a D-configuration furanose, the highest numbered chiral carbon is facing upwards.

The furanose ring will have either alpha or beta configuration, depending on which direction the anomeric hydroxy group is pointing. In a d-configuration furanose, alpha configuration has the hydroxy pointing down, and beta has the hydroxy pointing up. It is the opposite in an l-configuration furanose. Typically, the anomeric carbon undergoes mutarotation in solution, and the result is an equilibrium mixture of alpha-beta configurations.

References

^ Reginald, Garrett; Grisham M., Charles. (2005). Biochemistry 3rd Edition. Cengage Learning. ISBN 0-534-49033-6. ISBN 9780534490331.

English Journal

PCR Amplification of 4'-ThioDNA Using 2'-Deoxy-4'-thionucleoside 5'-Triphosphates.

Kojima T, Furukawa K, Maruyama H, Inoue N, Tarashima N, Matsuda A, Minakawa N.SourceGraduate School of Pharmaceutical Sciences, The University of Tokushima , Shomachi 1-78-1, Tokushima 770-8505, Japan.
ACS synthetic biology.ACS Synth Biol.2013 Sep 20;2(9):529-36. doi: 10.1021/sb400074w. Epub 2013 Aug 19.
2'-Deoxy-4'-thioribonucleic acid (4'-thioDNA) having a sulfur atom instead of an oxygen atom in the furanose ring has a nuclease resistance and hybridization ability higher than that of natural DNA. Despite its great potential for various biological applications, a long 4'-thioDNA having all four ki
PMID 23957635

β-Oxygen Effect in the Barton-McCombie Deoxygenation Reaction: Further Experimental and Theoretical Findings.

Sánchez-Eleuterio A, Sandoval-Lira J, García-Sánchez J, Monterrosas-Pérez L, Hernández-Pérez JM, Quintero L, Sartillo-Piscil F.SourceFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP) . 14 Sur Esq. San Claudio, San Manuel.72570, Puebla, México.
The Journal of organic chemistry.J Org Chem.2013 Sep 20;78(18):9127-36. doi: 10.1021/jo4012943. Epub 2013 Sep 9.
The chemistry of (S)-methyl xanthates derived from xylo- and ribo-furanose derivatives in the presence of the stannyl radical is investigated. Xanthate derived from β-xylo-furanose affords exclusively a deoxygenated product; whereas, under the same reaction conditions, the α-ribo-furanose xanthate
PMID 23987098

Synthesis of 3,6-O-(o-Xylylene)glucopyranosyl Fluoride, an Axial-Rich Glycosyl Donor of β-Glycosylation.

Asakura N, Motoyama A, Uchino T, Tanigawa K, Yamada H.SourceSchool of Science and Technology, Kwansei Gakuin University , 2-1 Gakuen, Sanda 669-1337, Japan.
The Journal of organic chemistry.J Org Chem.2013 Sep 20;78(18):9482-7. doi: 10.1021/jo401395h. Epub 2013 Sep 11.
Despite the reported complete β-selectivity in glycosylation with 2,4-di-O-benzyl-3,6-O-(o-xylylene)glucopyranosyl fluoride, its preparation has been inefficient. This paper describes an improved route for the donor, including the formation of the 3,6-bridge on 1,2,4-orthoacetylglucose, the prepara
PMID 23984627

Japanese Journal

フラノースグリコシドの化学合成

IMAMURA Akihiro,LOWARY Todd
Trends in glycoscience and glycotechnology 23(129), 134-152, 2011-05-31
多くの細菌類、真菌類、寄生虫、植物はO-フラノシド結合含有グリカンを産生する。これらの複合糖質はそれら生物の生存において不可欠である場合が多く、近年、フラノース含有糖鎖の化学的合成に着目した研究は増加の一途を辿っている。しかしながら、その合成研究分野の発展はピラノースグリコシドのそれと比較して決して十分とは言えない。本稿では、フラノースグリコシド合成において内在する課題を明らかにすると共に、これま …
NAID 10029582933

P-68 Pd(II)触媒を用いた新規ヘテロ環構築法の開発と糖類の合成(ポスター発表の部)

宮澤眞宏,内田雄輔,矢野祐介,吉田理恵,恩田一史,横山初,平井美朗
天然有機化合物討論会講演要旨集 (48), 649-654, 2006-09-15
… To demonstrate the synthetic potential of this method, we have synthesized furanose derivatives. …
NAID 110006682729

分子モデリングを用いた糖の抽出挙動の定量的構造物性相関

吉塚和治,松本道明,近藤和生
化学工学論文集 32(1), 6-10, 2006-01-20
生理活性物質の一つである糖のフェニルホウ酸と四級アンモニウム塩を用いた抽出分離に計算化学的手法を応用した．まず半経験的分子軌道計算に基づきフェニルホウ酸と単糖類の水相での錯体の生成熱を計算し，実測した安定度定数と比較した．この場合，ピラノース（六員環）型あるいはフラノース（五員環）型のいずれの構造の糖がフェニルホウ酸との錯形成に寄与しているかは明確にはできなかったが，その糖との選択性の順序は十分に …
NAID 130000018579