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

为了阐明mugineacid - fe （III）配合物的质膜转运体的分子结构，本研究首次合成了一些mugineacid类似物。(1)以-丁内酯、l -高丝氨酸和甘氨酸为原料，在NaBH_3CN存在下，通过还原偶联法制备了3′(S) - n -[3-羧基-（3-羧基丙基氨基）丙基]甘氨酸。在NaBH_3CN的存在下，用受保护的L-N-(3-羧基-（3-羧基丙基氨基）丙基]同丝氨酸醛与l -同丝氨酸内酯缩合合成了2 (S), 3′(S) - n -[3-羧基-（3-羧基丙基）丙基]同丝氨酸。(2)在NaBH_3CN存在下，通过甘氨酸和2分子l -高丝氨酸内酯三个单元的还原偶联，合成了3′(S), 3′(S) - n -[3-羧基-（3-氨基-3-羧基丙基氨基）丙基]甘氨酸。2 (S), 3’(S), 3’(S), 3’（S) - n -[3-羧基-（3-氨基-3-羧基丙基）丙基]同丝氨酸在NaBH_3CN存在下，以同样的方法将受保护的3’(S) - n -[3-氨基-3-羧基）同丝氨酸醛与l -家氨酸内酯缩合合成。(3)在NaBH_3CN的存在下，用还原缩合法合成了3′(S), 3′(S) - n -[3-羧基-（3-羧基-3-羟丙基）氨基丙基]甘氨酸。l -苹果酸制备的l - α -羟基- γ -丁内酯，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-羧基-3-羟丙基）氨基丙基]甘氨酸与d -苹果酸在NaBH_3CN存在下制备的d - α -羟基- γ -丁内酯缩合而成。

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.