有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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74 巻, 3 号
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  • 糖質化学への出会いから素人仕事の糖鎖生物学へ
    伊藤 幸成
    2016 年 74 巻 3 号 p. 206-218
    発行日: 2016/03/01
    公開日: 2016/05/17
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.206
    ジャーナル 認証あり
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    Carbohydrates are important constituents of biomolecules and natural products. In particular, glycoproteins, glycolipids, proteoglycans and cell-surface glycoconjugates are known to play various roles in biologically important phenomena. In spite of that, precise analysis of their functions has been hindered by their structural diversity and complexity. Synthetic organic chemistry is considered to be powerful in solving problems associated with their biological functions. Under such circumstances, major part of research in our group has been directed to the synthesis and functional analysis of glycoconjugate oligosaccharides of various origins. This account aims to summarize my research history in carbohydrate chemistry, which mainly covers 1) development of methodologies for oligosaccharide synthesis, 2) approaches to stereoselective glycoside bond formation, 3) synthetic studies on glycoconjugate glycan chains, and 4) analyses of glycoprotein processing and protein quality control system, and 5) studies on carbohydrate binding natural products.
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  • ジカチオン性パラジウム錯体を用いたフルオロアルキル化合物の触媒的不斉合成
    相川 光介, 三上 幸一
    2016 年 74 巻 3 号 p. 219-232
    発行日: 2016/03/01
    公開日: 2016/05/17
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.219
    ジャーナル 認証あり
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    By virtue of the unique properties of fluorine atom, fluorinated organic compounds often affect pharmaceutical and agrochemical industry. Over the past decades, a variety of methodology for incorporating fluoroalkyl groups, especially trifluoromethyl group, have been developed. On the other hand, the building-block methodology employing readily available fluoroalkyl-containing substances plays a prominent role in catalytic asymmetric synthesis of chiral fluoroalkylated compounds. Thus, chiral α-fluoroalkylated tertiary alcohols have received increasingly attention in the field of pharmaceutical science. A number of non-steroidal glucocorticoid receptor modulators bearing the chiral α-fluoroalkylated tertiary alcohols were found to possess anti-inflammatory effects of a glucocorticoid but with reduced adverse effects, and hence have been searched as potential therapeutics for various inflammatory diseases, such as asthma, rheumatoid arthritis, and allergic rhinitis. In this paper, we describe the development of practical synthetic methods of valuable and multi-functionalized derivatives of chiral α-fluoroalkyl substituted tertiary alcohol and these analogues.
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  • 光学活性な超原子価ヨウ素（III）によるアルケンの不斉酸化
    藤田 守文
    2016 年 74 巻 3 号 p. 233-242
    発行日: 2016/03/01
    公開日: 2016/05/17
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.233
    ジャーナル 認証あり
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    This article highlights my recent studies on development of optically active hypervalent iodine(III) reagents which have a chiral side chain derived from lactic acid. The lactate chiral side chain may nucleophilically interact with the iodine atom, and the interaction induces pseudo chirality of the iodine atom. Owing to the pseudo chirality, the iodine(III) reagent is able to highly distinguish the enantioface of an alkene substrate. Actually, the lactate-based hypervalent iodine(III) reagents have been used for various types of enantioselective oxidation leading to high ee. One of the stereoselective oxidations is applied to a crucial step for the asymmetric synthesis of 4-oxyisochroman-1-one natural products.
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  • イオンペア集合体を形成するアニオン応答性π電子系の合成
    羽毛田 洋平, 山門 陵平, 前田 大光
    2016 年 74 巻 3 号 p. 243-253
    発行日: 2016/03/01
    公開日: 2016/05/17
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.243
    ジャーナル 認証あり
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    A variety of anion-responsive π-electronic systems (anion receptors) based on a 1,3-dipyrrolylpropane-1,3-dione framework have been synthesized. The anion receptors form complexes with anions, affording diverse modes including [1+1]-type planar complexes. Anion complexes of the π-electronic systems form ion pairs with cationic species, resulting in assembled structures. Through interionic interactions and other noncovalent interactions, ion-pairing assemblies construct ordered structures in bulk materials such as crystals, supramolecular gels, and thermotropic liquid crystals, exhibiting fascinating electronic properties including semiconductive behaviors.
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  • meta-エチニルピリジンポリマー・オリゴマーの機能化によるらせん構造の安定化
    阿部 肇, 大石 雄基, 井上 将彦
    2016 年 74 巻 3 号 p. 254-265
    発行日: 2016/03/01
    公開日: 2016/05/17
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.74.254
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    We have developed poly- and oligo(2,6-pyridylene ethynylene)s, called as “meta-ethynylpyridine polymers/oligomers”, consisted of pyridine rings linked with acetylene bonds at the 2,6-positions. These foldamers are able to bind with saccharides by multipoint hydrogen bonding to form helical complexes. For further application of the helices, stabilization of the helicity is required. Herein we describe, roughly divided, three types of strategy to stabilize the helical structures. Those are (1) applying intramolecular glycoside templates, (2) coordinating between pitches from outside or inside of the helix, and (3) utilization of new pyridine-phenol alternating architecture to efficiently stabilize cisoid conformation. Interesting behavior of the stabilized helices was reported, in terms of chiral memory, strong saccharide recognition, and so on.
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