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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4-氧-L-脯氨酸氢溴酸盐 | 4-Oxopyrrolidine-2-carboxylic acid;hydrobromide | 75776-67-9 | C5H8BrNO3 |
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4-[(3-氯苯基)甲基]-l-脯氨酸盐酸盐 | (2S,4R)-4-(3-Chlorobenzyl)pyrrolidine-2-carboxylic acid hydrochloride | 1049733-75-6 | C12H15Cl2NO2 |
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3-苯基-L-脯氨酸 | 3-phenylproline | 118758-48-8 | C11H13NO2 |
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3,4-脱氢脯氨酸甲氧基酯盐酸盐 | H-3,4-dehydro-Pro-OMe*HCl | 186145-08-4 | C6H9NO2*ClH |
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3,4-脱氢-L-脯氨酸盐酸盐 | (S)-2,5-Dihydro-1H-pyrrole-2-carboxylic acid hydrochloride | 201469-31-0 | C5H8ClNO2 |
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3,4-脱氢-L-脯氨酸 | 3,4-dehydro-L-proline | 4043-88-3 | C5H7NO2 |
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3,4-脱氢-DL-脯氨酸 | DL-3,4-Dehydroproline | 3395-35-5 | C5H7NO2 |
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2-苄基-D-脯氨酸盐酸盐 | (S)-2-Benzylpyrrolidine-2-carboxylic acid hydrochloride | 637020-57-6 | C12H16ClNO2 |
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2-甲基-D-脯氨酸甲酯盐酸盐 | (R)-methyl 2-methylpyrrolidine-2-carboxylate hydrochloride | 1286768-32-8 | C7H13NO2*ClH |
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2-烯丙基-1-boc-2-吡咯烷羧酸 | 2-allyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid | 315234-49-2 | C13H21NO4 |
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2,4,5-三氯苯基 5-氧代-L-脯氨酸酯 | L-pyroglutamic acid 2,4,5-trichlorophenyl ester | 5910-47-4 | C11H8Cl3NO3 |
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2,2-二甲基-3-羰基-吡咯啉-1-羧酸乙酯 | ethyl 2,2-dimethyl-3-oxopyrrolidine-1-carboxylate | 106556-66-5 | C9H15NO3 |
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1-苄基-吡咯烷-2-羧酸 | N-benzyl proline | 60169-72-4 | C12H15NO2 |
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1-苄基-L-脯氨酸 | N-benzyl-L-proline | 31795-93-4 | C12H15NO2 |
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1-甲基-5-氧代脯氨酸甲酯 | methyl N-methylpyroglutamate | 190783-99-4 | C7H11NO3 |
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1-甲基-5-氧代-L-脯氨酸甲酯 | (S)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate | 42435-88-1 | C7H11NO3 |
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1-甲基-5-氧代-D-脯氨酸甲酯 | N-methyl D-5-oxoproline methyl ester | 122742-14-7 | C7H11NO3 |
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1-叔丁氧羰基-(4R)-羟基-2-脯氨酸乙脂 | 1-(tert-butyl) 2-ethyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate | 37813-30-2 | C12H21NO5 |
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1-丙脯氨酸 | 1-Propionylpyrrolidine-2-carboxylic acid | 59785-64-7 | C8H13NO3 |
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1-[N-[N-[9H-芴-9-基甲氧羰基]-L-丙氨酰]-L-丙氨酰]-L-脯氨酸 | Fmoc-Ala-Ala-Pro | 161220-53-7 | C26H29N3O6 |
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1-[1-[(9H-芴-9-基甲氧基)羰基]-L-脯氨酰]-D-脯氨酸 | (S)-1-((S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid | 144575-00-8 | C25H26N2O5 |
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1-N-Cbz-4-羟基-b-脯氨酸 | 1-benzyloxycarbonyl-4-hydroxypyrrolidine-3-carboxylic acid | 886362-64-7 | C13H15NO5 |
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1-BOC-2-甲基-DL-脯氨酸 | 1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid | 203869-80-1 | C11H19NO4 |
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1-(甲氧羰基)-L-脯氨酸 | (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid | 74761-41-4 | C7H11NO4 |
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1-(3-(三氟甲基)苯磺酰基)脯氨酸 | ((3-(trifluoromethyl)phenyl)sulfonyl)proline | 251096-97-6 | C12H12F3NO4S |
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1-(1-氧代十六烷基)-L-脯氨酸 | N-palmitoyl-L-proline | 59441-32-6 | C21H39NO3 |
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1-(1,2-二氧代-3,3-二甲基戊基)-L脯氨酸-(3-吡啶基)-丙酯 | 3-(3-pyridyl)-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-pyrrolidinecarboxylate | 186452-09-5 | C20H28N2O4 |
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(S)-二甲基吡咯烷-1,2-二甲酸基酯 | N-methoxycarbonyl-L-proline methyl ester | 83541-81-5 | C8H13NO4 |
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(S)-2-甲基脯氨酸 | (S)-2-methylpyrrolidine-2-carboxylic acid | 42856-71-3 | C6H11NO2 |
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(S)-1-苯甲基-N-BOC-DL-脯氨酸 | BOC-(S)-alpha-benzyl-proline | 706806-61-3 | C17H23NO4 |
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(R)-2-甲基脯氨酸 | (R)-2-methylpyrrolidine-2-carboxylic acid | 63399-77-9 | C6H11NO2 |
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(R)-1-苯甲基-N-BOC-DL-脯氨酸 | (R)-2-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid | 706806-60-2 | C17H23NO4 |
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(R)-1-甲基-4-羟基-L-脯氨酸甲酯 | methyl (2S,4R)-4-hydroxy-1-methyl-pyrrolidine-2-carboxylate | 13135-69-8 | C7H13NO3 |
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(R)-1-(叔丁氧基羰基)-4-氧代吡咯烷-2-羧酸 | (R)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid | 364077-84-9 | C10H15NO5 |
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(4S)-4-羟基-L-脯氨酸甲酯 | cis-L-hydroxyproline methyl ester | 81102-38-7 | C6H11NO3 |
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(4S)-4-甲基-l-脯氨酸 | cis-4-methyl-L-proline | 6734-41-4 | C6H11NO2 |
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(4R)-4-羟基-1-亚硝基-L-脯氨酸 | (4R)-hydroxy-1-nitroso-L-pyrrolidine-2-carboxylic acid | 30310-80-6 | C5H8N2O4 |
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(4R)-4-氟-1-{[(2-甲基-2-丙基)氧基]羰基}-D-脯氨酸 | (4R)-1-(tert-butoxycarbonyl)-4-fluoro-D-proline | 681128-51-8 | C10H16FNO4 |
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(4R)-4-叠氮-1-BOC-D-脯氨酸苄酯,(4R)-4-AZIDO-1-BOC-D-PROLINEBENZYLESTER | (4R)-1-(tert-butoxycarbonyl)-4-azido-D-proline benzyl ester | 132622-97-0 | C17H22N4O4 |
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(4R)-1-BOC-4-叠氮-L-脯氨酸乙酯,(4R)-1-BOC-4-AZIDO-L-PROLINEETHYLESTER | (4R)-1-(tert-butoxycarbonyl)-4-azido-L-proline ethyl ester | 132623-04-2 | C12H20N4O4 |
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(4R)-(叔丁氧基)-1-(苯甲氧羰基)-L-脯氨酸 | (2S,4R)-4-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester | 85201-91-8 | C17H23NO5 |
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(3R)-3-羟基-L-脯氨酸甲酯三氟乙酸盐 | (2S,3R)-methyl 3-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate | 496841-09-9 | C8H10F3NO4 |
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(2S,4r)-4-boc-氨基吡咯烷-2-羧酸甲酯 | 4-tertbutyloxycarbonylamino-L-trans-proline methyl ester | 473806-21-2 | C11H20N2O4 |
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(2S,4r)-1-boc-4-甲磺酰氧基脯氨酸 | (2S,4R)-1-(tert-butoxycarbonyl)-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylic acid | 202477-59-6 | C11H19NO7S |
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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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