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:
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。
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。
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。
实例
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 |
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(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 |
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(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 |
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(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 |
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(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 |
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(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 |
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(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 |
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(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 |
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(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 |
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(2R,4S)-4-氟-D-脯氨酸甲酯 | (2R,4S)-4-Fluoro-D-proline methyl ester | 732957-04-9 | C6H10FNO2 |
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(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 |
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—— | Glycyl-L-proline 7-amido-4-methylcoumarin hydrobromide | 115035-46-6 | C17H20BrN3O4 |
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—— | (R)-Dimethyl pyrrolidine-1,2-dicarboxylate | 374077-91-5 | C8H13NO4 |
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—— | 2-Pyrrolidon-5-carbonsaeure-2,4,5-trichlorphenylester | 5910-47-4 | C11H8Cl3NO3 |
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—— | (rac)-4-benzyloxy-2-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester | 54631-81-1 | C18H25NO5 |
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—— | N-benzoyl-cis-4-hydroxy-D-proline methyl ester | 120806-96-4 | C13H15NO4 |
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—— | HCl*Hyp-OBzl | 62147-27-7 | C12H15NO3*ClH |
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—— | 4-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid methyl ester | 13135-69-8 | C7H13NO3 |
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—— | 1-[3-(Acetylsulfanyl)-2-methylpropanoyl]pyrrolidine-2-carboxylate | 64838-55-7 | C11H16NO4S- |
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—— | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | 15761-39-4 | C10H16NO4 |
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—— | Sodium lauroyl proline | 70609-63-1 | C17H30NNaO3 |
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—— | 1-(1-Oxohexadecyl)-L-proline sodium salt | 58725-33-0 | C21H38NNaO3 |
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—— | (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 |
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—— | 4S-O<sup>4</sup>(t-butyl)-N1-(fluorenylmethyloxycarbonyl)-D-proline | 464193-92-8 | C24H27NO5 |
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—— | 2,5-Dioxopyrrolidin-1-yl 1-(tert-butoxycarbonyl)prolinate | 3392-10-7 | C14H20N2O6 |
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—— | 1-Ξ-alanyl-L-proline | 3918-95-4 | C8H14N2O3 |
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—— | (2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid; hydrobromide | 105107-84-4 | BrH*C11H13NO2S |
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—— | (R)-α-benzylproline | 86116-84-9 | C12H15NO2 |
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—— | 4-[(2-methylpropan-2-yl)oxy]pyrrolidin-1-ium-2-carboxylate | 79775-07-8 | C9H17NO3 |
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—— | (2S)-1-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylate | 64838-55-7 | C11H19NO5S |
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—— | (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester | 88043-21-4 | C19H27NO7S |
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—— | (2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-[(2-methylpropan-2-yl)oxy]pyrrolidine-2-carboxylate | 122996-47-8 | C24H26NO5- |
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—— | Sodium 1-hexadecanoyl-5-oxopyrrolidine-2-carboxylate | 58725-33-0 | C21H36NNaO4 |
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—— | 1-(2-aminoacetyl)-N-(4-methoxynaphthalen-2-yl)pyrrolidine-2-carboxamide | 42761-76-2 | C18H21N3O3 |
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—— | 4-oxo-L-proline ; hydrobromide | 75776-67-9 | BrH*C5H7NO3 |
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—— | 1,2-Dimethyl pyrrolidine-1,2-dicarboxylate | 73689-73-3 | C8H13NO4 |
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—— | N-lauroylproline | 58725-39-6 | C17H31NO3 |
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—— | N-phenylacetylproline | 2752-38-7 | C13H15NO3 |
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—— | N-palmitoyl-L-hydroxyproline | 41736-92-9 | C21H39NO4 |
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—— | Fmoc-Hyp-OH | 88050-17-3 | C20H19NO5 |
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—— | (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid | 130930-25-5 | C13H15NO5 |
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—— | methyl (2S,4R)-4-hydroxy-1-tosylpyrrolidine-2-carboxylate | 16257-57-1 | C13H17NO5S |
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—— | N-Cbz-trans-4-hydroxy-L-proline ethyl ester | 103667-57-8 | C15H19NO5 |
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—— | betainium L-pyroglutamate | 4810-57-5 | C5H6NO3*C5H12NO2 |
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—— | <i>cis</i>-1-acetyl-4-hydroxy-DL-proline | 33996-33-7 | C7H11NO4 |
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—— | N-(tert-butoxycarbonyl)-D-proline | 37784-17-1 | C10H17NO4 |
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—— | (S)-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid | 14296-92-5 | C12H20N2O5 |
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—— | N-tert-butoxycarbonyl-proline | 15761-39-4 | C10H17NO4 |
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—— | 3-hydroxy-dl-proline | 51-35-4 | C5H9NO3 |
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—— | N-carbobenzyloxyproline | 1148-11-4 | C13H15NO4 |
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—— | Tryptophyl-Proline | 38136-75-3 | C16H19N3O3 |
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