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Study on a specific recognition mechanism for mugineic acid-Fe (III) complex in gramineous plants

禾本科植物麦根酸-Fe(III)络合物特异性识别机制研究

基本信息

批准号：
07680642
负责人：
NOMOTO Kyosuke
金额：
$ 1.47万
依托单位：
Suntory Institute for Bioorganic Research (SUNBOR)
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1995
资助国家：
日本
起止时间：
1995 至 1997
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07680642/
关键词：
Mugineic Acids Phytosiderophores Chelators Gramineous Plants

项目摘要

In order to elucidate a molecular structure of plasma membrane-located transporter for mugineic acid-Fe (III) complex, a few mugineic acid analogs were first synthesized in the present study.(1) The systhesis of 3'(S) -N- [3-carboxy- (3-carboxypropylamino) propyl] glycine was performed by reductive coupling in the presence of NaBH_3CN of three units, i.e., gamma-butyrolactone, L-homoserine, and glycine. In a similar manner as above, 2 (S), 3'(S) -N- [3-carboxy- (3-carboxypropylamino) propyl] homoserine was synthesized by the condensation of the protected L-N- (3-carboxyprpyl) homeserine aldehyde with L-homoserine lactone in the presence of NaBH_3CN.(2) The synthesis of 3'(S), 3"(S) -N- [3-carboxy- (3-amino-3-carboxypropylamino) propyl] glycine was achieved by reductive coupling in the presence of NaBH_3CN of three units, namely glycine and 2 molecular L-homoserine lactone. 2 (S), 3'(S), 3"(S) -N- [3-carboxy- (3-amino-3-carboxypropylamino) propyl] homo-serine was similarly synthesized by the condensation of the protected 3'(S) -N- [3-amino-3-carboxyprpyl) homoserine aldehyde with L-homeserine lactone in the presence of NaBH_3CN.(3) Furthermore, the synthesis of 3'(S), 3"(S) -N- [3-carboxy- (3-carboxy-3-hydroxypropyl) aminopropyl] glycine was carried out by reductive condensation in the presence of NaBH_3CN of three units, ie., L-alpha-hydroxy-gamma-butyrolactone prepared from L-malic acid, L-homoserine aldehyde derived from L-aspartic acid and glycine. 3'(S), 3"(R) -N- [3-carboxy- (3-carboxy-3-hydroxypropyl) aminopropyl] glycine was similarly synthesized by the condensation of the protected 3'(S) -N- (3-carboxy-3-aminopropyl) glycine with D-alpha-hydroxy-gamma-butyrolactone prepared from D-malic acid in the presence of NaBH_3CN.

为了阐明芥子酸-Fe(III)络合物的细胞膜转运蛋白的分子结构，本研究首次合成了几个芥酸类似物：(1)以γ-丁内酯、L-高丝氨酸和甘氨酸为三个单元，在NaBH_3CN存在下，还原偶联合成了3‘(S)-N-[3-羧基-(3-羧丙氨基)丙基]甘氨酸。以同样的方法，通过保护的S-N-(3-羧丙氨基)高丝氨酸甲醛与L-高丝氨酸内酯在NaBH_3CN存在下进行缩合反应，合成了2(S)，3‘(S)-N-[3-羧基-(3-羧丙氨基)丙基]高丝氨酸。(2)3’(S)，3“(S)-N-[3-羧基-(3-氨基-3-羧丙氨基)丙基]甘氨酸的合成。即甘氨酸和2个分子的L-高丝氨酸内酯。2(S)，3‘(S)，3“(S)-N-[3-羧基-(3-氨基-3-羧丙氨基)丙基]高丝氨酸类似地被保护的3’(S)-N-[3-氨基-3-羧丙基)高丝氨酸醛与L-高丝氨酸内酯在NaBH_3CN存在下缩合而得。(3)3‘(S)的合成，3“(S)-N-[3-羧基-(3-羧基-3-羟丙基)氨基丙基]甘氨酸在三个单元的NaBH_3CN存在下还原缩合得到3”(L)-N-[3-羧基-(3-羧基-3-羟丙基)氨基丙基]甘氨酸，即由L-苹果酸制得的L-α-羟基-γ-丁内酯，由L-天冬氨酸和甘氨酸衍生的L-高丝氨酸醛。3‘(S)，3“(R)-N-[3-羧基-(3-羟丙基)氨丙基]甘氨酸与以D-苹果酸为原料制得的D-α-羟基-γ-丁内酯在NaBH3CN存在下经缩合反应合成了3’(S)，3”(R)-N-[3-羧基-3-羟丙基]甘氨酸。