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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N-苄氧羰基-2-甲基-D-脯氨酸 | Z-D-(αMe)-Pro-OH | 63399-74-6 | C14H17NO4 |
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N-苄基-L-脯氨酸乙酯 | N-benzyl-L-proline ethyl ester | 955-40-8 | C14H19NO2 |
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N-苄基-D-脯氨酸乙酯 | (R)-N-benzylproline ethyl ester | 172478-10-3 | C14H19NO2 |
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N-芴甲氧羰基-脯氨酰-脯氨酸 | Fmoc-Pro-Pro-OH | 129223-22-9 | C25H26N2O5 |
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N-芴甲氧羰基-L-脯氨酸4-硝基苯酯 | Fmoc-Pro-ONp | 71989-32-7 | C26H22N2O6 |
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N-芴甲氧羰基-4-哌啶基-L-脯氨酸 | (2S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(piperidin-1-yl)pyrrolidine-2-carboxylic acid | 204318-02-5 | C25H28N2O4 |
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N-甲基-L-脯氨酸 | N-methyl-L-proline | 475-11-6 | C6H11NO2 |
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N-甲基-D-脯氨酸盐酸盐 | N-methyl-D-proline hydrochloride | 702710-17-6 | C6H11NO2*ClH |
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N-甲基-D-脯氨酸一水合物 | N-Methyl-D-proline monohydrate | 1217447-61-4 | C6H13NO3 |
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N-叔丁氧羰基-反-4-N-芴甲氧羰基-氨基-L-脯氨酸 | (2S,4R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid | 176486-63-8 | C25H28N2O6 |
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N-叔丁氧羰基-O-苄基-反式-4-羟基-L-脯氨酸 | (2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid | 54631-81-1 | C17H23NO5 |
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N-十四碳酰基-L-脯氨酸 | N-tetradecanoyl-L-proline | 86282-96-4 | C19H35NO3 |
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N-十六碳酰基-4-羟基-L-脯氨酸 | palmitoyl hydroxyproline | 41736-92-9 | C21H39NO4 |
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N-十二碳酰基-L-脯氨酸 | N-dodecanoyl-L-proline | 58725-39-6 | C17H31NO3 |
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N-乙酰-L-脯氨酸 | (S)-acetylproline | 68-95-1 | C7H11NO3 |
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N-乙酰-L-硫代脯氨酸 | (4R)-3-acetyl-4-thiazolidinecarboxylic acid | 54323-50-1 | C6H9NO3S |
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N-乙酰-L-4-羟基脯氨酸 | oxaceprol | 33996-33-7 | C7H11NO4 |
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N-乙酰-D-脯氨酸 | N-acetyl-D-proline | 59785-68-1 | C7H11NO3 |
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N-cbz-4-氧-L-脯氨酸 | 1-benzyloxycarbonyl-4-keto-L-proline | 64187-47-9 | C13H13NO5 |
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N-[叔丁氧羰基]甘氨酰-L-脯氨酸 | (tert-butoxycarbonyl)glycylproline | 14296-92-5 | C12H20N2O5 |
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N-Z-L-脯氨酸甲酯 | N-carbobenzyloxy-L-proline methyl ester | 5211-23-4 | C14H17NO4 |
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N-Fmoc-反式-4-羟基-L-脯氨酸甲酯 | Fmoc-Hyp-OMe | 122350-59-8 | C21H21NO5 |
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N-Cbz-L-脯氨酸叔丁酯 | (S)-2-tert-butyl-1-benzylpyrrolidine-1,2-dicarboxylate | 16881-39-3 | C17H23NO4 |
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N-CBZ-顺式-L-羟脯氨酸甲酯 | (2S,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate | 57653-35-7 | C14H17NO5 |
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N-CBZ-顺式-4-羟基-D-脯氨酸甲酯 | (2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate | 155075-23-3 | C14H17NO5 |
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N-CBZ-羟脯氨酸甲酯 | methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate | 64187-48-0 | C14H17NO5 |
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N-CBZ-反式-4-氨基-L-脯氨酸甲酯盐酸盐 | methyl (2S,4R)-4-amino-1-[benzyloxycarbonyl]pyrrolidine-2-carboxylate hydrochloride | 409325-33-3 | C14H18N2O4*ClH |
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N-CBZ-4-氧-L-脯氨酸甲酯 | 1-benzyloxycarbonyl-4-oxo-<i>L</i>-proline methyl ester | 16217-15-5 | C14H15NO5 |
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N-Boc-顺式-4-羟基-L-脯氨酸甲酯 | (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester | 102195-79-9 | C11H19NO5 |
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N-Boc-顺式-4-羟基-L-脯氨酸 | N-tert-butoxycarbonyl-L-cis-4-hydroxyproline | 87691-27-8 | C10H17NO5 |
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N-Boc-顺式-4-羟基-D-脯氨酸 | (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline | 135042-12-5 | C10H17NO5 |
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N-Boc-顺式-4-氟-L-脯氨酸甲酯 | 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate | 475561-81-0 | C11H18FNO4 |
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N-Boc-顺式-4-Fmoc-氨基-L-脯氨酸 | (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester | 174148-03-9 | C25H28N2O6 |
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N-Boc-反式-4-羟基-L-脯氨酸甲酯 | 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate | 74844-91-0 | C11H19NO5 |
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N-Boc-反式-4-羟基-D-脯氨酸 | (2R,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid | 147266-92-0 | C10H17NO5 |
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N-Boc-反式-4-氨基-L-脯氨酸甲酯盐酸盐 | (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester hydrochloride | 334999-32-5 | C11H20N2O4*ClH |
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N-Boc-反式-4-氨基-L-脯氨酸甲酯 | 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate | 121148-00-3 | C11H20N2O4 |
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N-Boc-反式-4-氟-L-脯氨酸甲酯 | 1-(tert-butyl) 2-methyl (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate | 203866-18-6 | C11H18FNO4 |
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N-Boc-反式-4-氟-L-脯氨酸 | (2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid | 203866-14-2 | C10H16FNO4 |
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N-Boc-反式-4-对甲苯磺酰氧基-L-脯氨酸甲酯 | 1-(tert-butyl) 2-methyl (2S,4R)-4-(tosyloxy)pyrrolidine-1,2-dicarboxylate | 88043-21-4 | C18H25NO7S |
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N-Boc-4-羰基-L-脯氨酸甲酯 | (R)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate | 256487-77-1 | C11H17NO5 |
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N-Boc-4-氧代-脯氨酸 | N-tert-butoxycarbonyl-4-oxo-L-proline | 84348-37-8 | C10H15NO5 |
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N-Boc-4-亚甲基-L-脯氨酸 | (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid | 84348-38-9 | C11H17NO4 |
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N-Boc-4,4-二氟-L-脯氨酸甲酯 | 1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate | 203866-17-5 | C11H17F2NO4 |
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N-Boc-4,4-二氟-L-脯氨酸 | 1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline | 203866-15-3 | C10H15F2NO4 |
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N-BOC-反式-4-羟基-D-脯氨酸甲酯 | (2R,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate | 135042-17-0 | C11H19NO5 |
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N-BOC-4-氧代-L-脯氨酸叔丁酯 | (S)-di-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate | 166410-05-5 | C14H23NO5 |
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N-BOC-4-亚甲基-L-脯氨酸甲酯 | (S)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate | 84348-39-0 | C12H19NO4 |
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N-BOC-2-甲基-L-脯氨酸 | N-(tert-butoxycarbonyl)-2-methyl-L-proline | 103336-06-7 | C11H19NO4 |
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N-BOC-(R)-1-(4-氟苄基)-DL-脯氨酸 | (R)-1-(tert-Butoxycarbonyl)-2-(4-fluorobenzyl)pyrrolidine-2-carboxylic acid | 706806-64-6 | C17H22FNO4 |
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