Optical resolution of pyridoxal-like pyridinophanes.
スポンサーリンク
概要
- 論文の詳細を見る
Racemic modifications of the pyridoxal-like ansa compounds such as 15-formyl-14-hydroxy-2,8-dithia[9](2,5)pyridinophanes prepared as a pontential catalyst for stereospecific nonenzymatic reactions were optically resolved through formation of Schiff bases by treatment with amino sugar derivatives or amino acids. Resolutions with the amino sugar derivatives were ascribable to the difference of the solubilities of the diastereomeric Schiff bases, whereas those with the amino acids resulted from the difference of the reaction rates for the formation of the diastereomeric Schiff bases. As the amino sugar resolving agents, 3-amino-3-deoxy-1,2:5,6-di-<I>O</I>-isopropylidene-β-D-idofuranose and the corresponding α-D-glucofuranose isomer were employed and gave (<I>R</I>)- and (<I>S</I>)-pyridoxal-like pyridinophanes, respectively. On the other hand, chiral valine was the most efficient resolving agent among the amino acid tested and the presence of half equimolar Fe<SUP>3+</SUP> markedly increased the optical purities of the products. Employment of (<I>S</I>)-valine gave (<I>R</I>)-pyridinophanes in excess and <I>vice versa</I>.
- 公益社団法人 日本化学会の論文
著者
-
Ando Makoto
The Institute of Physical and Chemical Research
-
Komatsu Toshihiko
The Institute of Physical and Chemical Research
-
Kuzuhara Hiroyoshi
The Institute of Physical and Chemical Research
-
Tachibana Yoji
The Institute of Physical and Chemical Research
関連論文
- Regioselective Mono-2-C-iodination of Fully Methylated Cyclodextrins through Interconversions between Cyclic and Acyclic Structures
- Facile Synthesis of 6^1-O-(α-D-Galactopyranosyl)cyclomaltoheptaose from Commercially Available Branched Cyclodextrin
- Efficient and Regioselective Preparation of an Eight-membered Interglycosidic Benzylidene Derivative of β-Cyclodextrin
- Synthesis of a New Allosamidin Analog, N,N'-Diacetyl-β-Chitobiosyl Allosamizoline, and Its Inhibitory Activity against Some Chitinases
- Catalytic activities of salicylaldehyde derivatives. V. Syntheses and catalytic activities of some trimethylammonio derivatives of salicylaldehyde in the racemization of L-glutamic acid.
- The use of Grignard reagents in the synthesis of carbohydrates. III. The one-way anomerization of methyl glycofuranosides and the opening of their furanose rings.
- Preferential introduction of a pyridylmethyl group into sulfonamides as an approach to an intramolular transimination.
- Asymmetric synthesis of .ALPHA.-deuterated .ALPHA.-amino acids through nonenzymatic transamination reaction and the determination of their enantiomeric excesses.
- Optical resolution of pyridoxal-like pyridinophanes.
- A kinetic study of a Zn2+-catalyzed transamination reaction between pyridoxamine analogs with a pyridinophane structure and .ALPHA.-keto acids.
- Catalytic Activities of Salicylaldehyde Derivatives. III. An Improved Synthesis of 6-Nitrosalicylaldehyde
- Catalytic activities of salicylaldehyde derivatives. VII. Synthesis and catalytic activity of (2-formyl-3-hydroxyphenyl)dimethylsulfonium salt in the racemization of L-glutamic acid.
- Chemistry of chiral vitamin B6 analogs. IV. Syntheses of chiral pyridoxal and pyridoxamine analogs having a branched "ansa chain" between 2'- and 5'-positions.