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脯氨酸类衍生物

脯氨酸是一类天然存在的α-氨基酸,因其独特的手性碳原子和环状结构,在有机合成、药物化学及材料科学中具有广泛应用。脯氨酸类衍生物主要包括以下几方面:

  1. 结构特征:脯氨酸的侧链包含一个四元氮杂环(吡咯环),这使得它在反应性和立体选择性上与普通α-氨基酸有所不同,常用于构建特定的空间构型和手性中心。

  2. 应用领域

    • 有机合成中的应用: 由于脯氨酸独特的化学性质,在不对称催化、模板诱导的化学转化中扮演重要角色。例如,在钯催化的氢化反应中,脯氨酸能够作为双膦配体使用。

    • 药物设计与开发: 脯氨酸衍生物被用作前药或直接用于药物分子的设计和合成中。其环状结构赋予了化合物特殊的物理化学性质,如增加水溶性、改善生物利用度等。

  3. 研究进展

    • 合成方法:近年来,通过不对称催化、光化学反应、过渡金属催化等先进手段制备脯氨酸衍生物的研究不断深入。

    • 生物医学应用:基于其独特的结构和性质,脯氨酸类化合物被探索用于治疗包括癌症、心血管疾病在内的多种疾病的潜在药物。例如,在抗癌领域中,某些含脯氨酸的多肽能够通过靶向肿瘤细胞发挥疗效。

  4. 实例

    • 脯氨酸及其衍生物在医药领域的一个重要应用是它们作为抗炎剂和免疫调节剂的作用机制研究。
    • 另外,基于脯氨酸骨架的新型抗生素、抗癌药物以及蛋白质稳定剂的研究正在逐步推进。

总体而言,脯氨酸类衍生物因其独特的化学性质和生物学活性,在多个科学与工业领域展现出巨大的潜力和应用前景。

中文名称 英文名称 CAS号 化学式 结构式图片
(2S,4S)-N-Boc-顺式-4-氟-L-脯氨酸 (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid 203866-13-1 C10H16FNO4
(2S,4S)-N-Boc-顺式-4-氟-L-脯氨酸
(2S,4S)-4-羟基-1,2-吡咯烷二甲酸 1-芴甲基酯 2-苄基酯 (2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-(9H-fluoren-9-ylmethyl) ester 439290-35-4 C27H25NO5
(2S,4S)-4-羟基-1,2-吡咯烷二甲酸 1-芴甲基酯 2-苄基酯
(2S,4S)-4-氟吡咯烷-2-羧酸盐酸盐 (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid hydrochloride 1001354-51-3 C5H8FNO2*ClH
(2S,4S)-4-氟吡咯烷-2-羧酸盐酸盐
(2S,4S)-1-叔丁基二甲基4-氨基吡咯烷-1,2二羧酸 N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester 84520-68-3 C11H18N4O4
(2S,4S)-1-叔丁基二甲基4-氨基吡咯烷-1,2二羧酸
(2S,4R)-Cbz-4-甲磺酰氧基脯氨酸甲酯 (2S,4R)-1-benzyl 2-methyl 4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate 117811-78-6 C15H19NO7S
(2S,4R)-Cbz-4-甲磺酰氧基脯氨酸甲酯
(2S,4R)-BOC-Γ-甲磺酰基氧甲基脯氨酸甲酯 1-(tert-butyl) 2-methyl (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate 84520-67-2 C12H21NO7S
(2S,4R)-BOC-Γ-甲磺酰基氧甲基脯氨酸甲酯
(2S,4R)-BOC-4-苯甲酰氧基脯氨酸甲酯 1-tert-butyl 2-methyl (2S,4S)-4-((benzoyl)oxy)-1,2-pyrrolidinedicarboxylate 121147-94-2 C18H23NO6
(2S,4R)-BOC-4-苯甲酰氧基脯氨酸甲酯
(2R,4S)-4-羟基吡咯烷-2-羧酸甲酯盐酸盐 (2R,4S)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride 481704-21-6 C6H11NO3*ClH
(2R,4S)-4-羟基吡咯烷-2-羧酸甲酯盐酸盐
(2R,4S)-4-氟-D-脯氨酸甲酯 (2R,4S)-4-Fluoro-D-proline methyl ester 732957-04-9 C6H10FNO2
(2R,4S)-4-氟-D-脯氨酸甲酯
(1S,2s,5r)-3-(叔丁氧基羰基)-3-氮杂双环 (1s,2s,5r)-3-(叔丁氧基羰基)-3-氮杂双环[3.1.0]己烷-2-羧酸 (1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 400720-05-0 C11H17NO4
(1S,2s,5r)-3-(叔丁氧基羰基)-3-氮杂双环 (1s,2s,5r)-3-(叔丁氧基羰基)-3-氮杂双环[3.1.0]己烷-2-羧酸
—— Glycyl-L-proline 7-amido-4-methylcoumarin hydrobromide 115035-46-6 C17H20BrN3O4
Glycyl-L-proline 7-amido-4-methylcoumarin hydrobromide
—— (R)-Dimethyl pyrrolidine-1,2-dicarboxylate 374077-91-5 C8H13NO4
(R)-Dimethyl pyrrolidine-1,2-dicarboxylate
—— 2-Pyrrolidon-5-carbonsaeure-2,4,5-trichlorphenylester 5910-47-4 C11H8Cl3NO3
2-Pyrrolidon-5-carbonsaeure-2,4,5-trichlorphenylester
—— (rac)-4-benzyloxy-2-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 54631-81-1 C18H25NO5
(rac)-4-benzyloxy-2-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
—— N-benzoyl-cis-4-hydroxy-D-proline methyl ester 120806-96-4 C13H15NO4
N-benzoyl-cis-4-hydroxy-D-proline methyl ester
—— HCl*Hyp-OBzl 62147-27-7 C12H15NO3*ClH
HCl*Hyp-OBzl
—— 4-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid methyl ester 13135-69-8 C7H13NO3
4-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid methyl ester
—— 1-[3-(Acetylsulfanyl)-2-methylpropanoyl]pyrrolidine-2-carboxylate 64838-55-7 C11H16NO4S-
1-[3-(Acetylsulfanyl)-2-methylpropanoyl]pyrrolidine-2-carboxylate
—— 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- 15761-39-4 C10H16NO4
1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-
—— Sodium lauroyl proline 70609-63-1 C17H30NNaO3
Sodium lauroyl proline
—— 1-(1-Oxohexadecyl)-L-proline sodium salt 58725-33-0 C21H38NNaO3
1-(1-Oxohexadecyl)-L-proline sodium salt
—— (2R,4S,5R)-1-(3-methoxy-4-tert-butylbenzoyl)-4-(methoxymethyl)-2-(1H-pyrazol-1-ylmethyl)-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid 885264-71-1 C26H32N4O5S
(2R,4S,5R)-1-(3-methoxy-4-tert-butylbenzoyl)-4-(methoxymethyl)-2-(1H-pyrazol-1-ylmethyl)-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid
—— 4S-O<sup>4</sup>(t-butyl)-N1-(fluorenylmethyloxycarbonyl)-D-proline 464193-92-8 C24H27NO5
4S-O<sup>4</sup>(t-butyl)-N1-(fluorenylmethyloxycarbonyl)-D-proline
—— 2,5-Dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate 3392-10-7 C14H20N2O6
2,5-Dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate
—— 1-Ξ-alanyl-L-proline 3918-95-4 C8H14N2O3
1-Ξ-alanyl-L-proline
—— (2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid; hydrobromide 105107-84-4 BrH*C11H13NO2S
(2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid; hydrobromide
—— (R)-α-benzylproline 86116-84-9 C12H15NO2
(R)-α-benzylproline
—— 4-[(2-methylpropan-2-yl)oxy]pyrrolidin-1-ium-2-carboxylate 79775-07-8 C9H17NO3
4-[(2-methylpropan-2-yl)oxy]pyrrolidin-1-ium-2-carboxylate
—— (2S)-1-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylate 64838-55-7 C11H19NO5S
(2S)-1-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylate
—— (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 88043-21-4 C19H27NO7S
(2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
—— (2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-[(2-methylpropan-2-yl)oxy]pyrrolidine-2-carboxylate 122996-47-8 C24H26NO5-
(2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-[(2-methylpropan-2-yl)oxy]pyrrolidine-2-carboxylate
—— Sodium 1-hexadecanoyl-5-oxopyrrolidine-2-carboxylate 58725-33-0 C21H36NNaO4
Sodium 1-hexadecanoyl-5-oxopyrrolidine-2-carboxylate
—— 1-(2-aminoacetyl)-N-(4-methoxynaphthalen-2-yl)pyrrolidine-2-carboxamide 42761-76-2 C18H21N3O3
1-(2-aminoacetyl)-N-(4-methoxynaphthalen-2-yl)pyrrolidine-2-carboxamide
—— 4-oxo-L-proline ; hydrobromide 75776-67-9 BrH*C5H7NO3
4-oxo-L-proline ; hydrobromide
—— 1,2-Dimethyl pyrrolidine-1,2-dicarboxylate 73689-73-3 C8H13NO4
1,2-Dimethyl pyrrolidine-1,2-dicarboxylate
—— N-lauroylproline 58725-39-6 C17H31NO3
N-lauroylproline
—— N-phenylacetylproline 2752-38-7 C13H15NO3
N-phenylacetylproline
—— N-palmitoyl-L-hydroxyproline 41736-92-9 C21H39NO4
N-palmitoyl-L-hydroxyproline
—— Fmoc-Hyp-OH 88050-17-3 C20H19NO5
Fmoc-Hyp-OH
—— (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 130930-25-5 C13H15NO5
(2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
—— methyl (2S,4R)-4-hydroxy-1-tosylpyrrolidine-2-carboxylate 16257-57-1 C13H17NO5S
methyl (2S,4R)-4-hydroxy-1-tosylpyrrolidine-2-carboxylate
—— N-Cbz-trans-4-hydroxy-L-proline ethyl ester 103667-57-8 C15H19NO5
N-Cbz-trans-4-hydroxy-L-proline ethyl ester
—— betainium L-pyroglutamate 4810-57-5 C5H6NO3*C5H12NO2
betainium L-pyroglutamate
—— <i>cis</i>-1-acetyl-4-hydroxy-DL-proline 33996-33-7 C7H11NO4
<i>cis</i>-1-acetyl-4-hydroxy-DL-proline
—— N-(tert-butoxycarbonyl)-D-proline 37784-17-1 C10H17NO4
N-(tert-butoxycarbonyl)-D-proline
—— (S)-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid 14296-92-5 C12H20N2O5
(S)-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid
—— N-tert-butoxycarbonyl-proline 15761-39-4 C10H17NO4
N-tert-butoxycarbonyl-proline
—— 3-hydroxy-dl-proline 51-35-4 C5H9NO3
3-hydroxy-dl-proline
—— N-carbobenzyloxyproline 1148-11-4 C13H15NO4
N-carbobenzyloxyproline
—— Tryptophyl-Proline 38136-75-3 C16H19N3O3
Tryptophyl-Proline