(3S,4R)-4-氨基-3-羟基-6-甲基庚酸 | 49642-11-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (3S,4R)-4-氨基-3-羟基-6-甲基庚酸
• 英文名称: (3S,4R)-4-amino-3-hydroxy-6-methylheptanoic acid
• 英文别名: (+/-)-erythro-statine；(3S,4R)-statine；anti-statine；(+)-(3S,4R)-AHMHA
• CAS: 49642-11-7
• 化学式: C₈H₁₇NO₃
• 分子量: 175.228
• InChiKey: DFVFTMTWCUHJBL-RQJHMYQMSA-N

物化性质

• 沸点：
  355.1±32.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3S,4R)-4-Azido-4-formyloxy-6-methylheptanal 在 钯 氢气 作用下， 以 甲醇 、 水 为溶剂， 生成 (3S,4R)-4-氨基-3-羟基-6-甲基庚酸
  参考文献：
  名称：

  (3S, 4S)-和 (3S, 4R)-4-Amino-3-hydroxy-6-methylheptanoic Acid 及其 N-(Acetyl-L-valyl-L-valyl) 衍生物的合成

  摘要：

  存在于胃蛋白酶抑制剂、酸性蛋白酶的特异性抑制剂及其 (+) (3S,4R) 非对映异构体 (10b) 中的天然 (-)(3S,4S)-4-氨基-3-羟基-6-inethylheptanoic 酸 (10a) 是从 3-deoxy-1,2-O-isopropylidene-α-D-erythro-pentodialdo-1,4-furanose (1) 通过高度立体选择性和立体特异性路线合成。胃酶抑素Ac、N-(乙酰基-L-缬氨酰-L-缬氨酰)-(3S,4S)-4-氨基-3-羟基-6-甲基庚酸(15a)及其(3S,4R)的部分肽非对映异构体 (15b) 是通过 10a 和 10b 的叔丁酯分别与乙酰基-L-缬氨酰-L-缬氨酸叠氮化物的叠氮偶联合成的。化合物15a抑制胃蛋白酶的蛋白水解，然而，非对映异构体15b对胃蛋白酶没有抑制作用。

  DOI：

  10.1246/bcsj.48.570

文献信息

• Synthesis of all the stereoisomers of statine (4-amino-3-hydroxy-6-methylheptanoic acid). Inhibition of pepsin activity by N-carbobenzoxy-L-valyl-L-valyl-statine derived from the four stereoisomers
  作者：W. S. Liu、S. C. Smith、G. I. Glover

  DOI：10.1021/jm00191a023

  日期：1979.5

  Synthesis of all four stereoisomers of the novel amino acid statine, 4-amino-3-hydroxy-6-methylheptanoic acid, found in pepstatin, a potent acid protease inhibitor, has been accomplished. Carbobenzoxy-L-valyl-L-valyl-statine tripeptides derived from all four stereoisomers have been prepared and their effect on pepsin activity is compared to that of pepstatin.

  已经完成了在强力蛋白酶抑制剂胃抑素中发现的新型氨基酸他汀（4-氨基-3-羟基-6-甲基庚酸）的所有四种立体异构体的合成。已经制备了衍生自所有四种立体异构体的碳苯并氧-L-戊基-L-戊基-他汀类三肽，并将其对胃蛋白酶活性的影响与胃酶抑素进行了比较。
• [EN] PHOSPHONAMIDATE ESTER-CONTAINING PSEUDOPEPTIDES
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1993009134A1

  公开（公告）日：1993-05-13

  (EN) A 'capped' phosphonamide C1-C6 alkyl ester linkage unit for joining peptides is disclosed. The linkage unit is substantially isosteric and isocoulombic as compared to conventional peptide backbone structures. The 'capping' of the phosphonamide by the C1-C6 alkyl ester causes the linkage unit to be acid stable. When incorporated into a peptide, the phosphonamide C1-C6 alkyl ester linkage unit becomes resistant to cleavage by aspartic proteinase. Accordingly, the phosphonamide C1-C6 alkyl ester linkage unit enhances and/or facilitates the aspartic proteinase inhibition activity of peptides into which it is incorporated.(FR) Une unité 'coiffée' de liaison à ester d'alkyle C1-C6 de phosphonamide est utile pour relier des peptides. L'unité de liaison est essentiellement isotérique et isocoulombienne par rapport aux squelettes peptidiques classiques. Le fait que le phosphonamide est 'coiffé' par l'ester d'alkyle C1-C6 rend l'unité de liaison stable aux acides. Lorsqu'elle est incorporée à un peptide, l'unité de liaison à ester d'alkyle C1-C6 de phosphonamide devient résistante au clivage par la protéinase aspartique. Par conséquent, l'unité de liaison à ester d'alkyle C1-C6 de phosphonamide améliore et/ou facilite l'activité d'inhibition de la protéinase aspartique des peptides auxquels elle est incorporée.

  一种连接肽的磷酸酰胺加成C1-C6甲基酯连接单元被揭示了。与传统肽骨架结构相比，该连接单元在等离子体和电荷方面是等离子体和电荷稳定的。磷酸酰胺的C1-C6甲基酯封口使连接单元呈现酸稳定特性。该连接单元被整合到肽中时，会使磷酸酰胺C1-C6甲基酯连接单元具有抵御蛋白酶box.slice增强的能力。因此，磷酸酰胺C1-C6甲基酯连接单元增强或促进整合到其中的肽的蛋白酶抑制活性。
• Unusual Regioselection in the Mitsunobu Reactions of <i>s</i><i>yn</i>-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer
  作者：Soo Y. Ko

  DOI：10.1021/jo015967f

  日期：2002.4.1

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.
• A simple total synthesis of naturally occurring hydroxy-amino acids by enzymatic kinetic resolution
  作者：Yang Lu、Christine Miet、Nicole Kunesch、Jacques E. Poisson

  DOI：10.1016/s0957-4166(00)80128-7

  日期：1993.5

  Both optically pure enantiomers of GABOB and isoserine were obtained by enzymatic kinetic resolution of acetylated precursors in three or four steps. The key intermediates were cyanohydrins available from simple aldehydes. This procedure can be applied to other unusual hydroxy amino acids widely distributed in biologically important peptides.
• General asymmetric synthesis of hydroxymethylene and hydroxyethylene peptide isosteres
  作者：Yutaka Aoyagi、Robert M. Williams

  DOI：10.1016/s0040-4020(98)00495-5

  日期：1998.8

  The Lewis acid-promoted coupling reactions of (5R, 6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6- diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazines (11a-e, and 21), which are prepared easily from (+)-(5R, 6S)-4- (benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (9), with allyltrimethylsilane proceeded to give the corresponding coupling products with moderate to excellent stereoselectivity in good yields. These coupling products (13a, b, and d) were converted to hydroxymethylene- (25a, b, and d) and hydroxyethylene (28) peptide isosteres. (C) 1998 Elsevier Science Ltd. All rights reserved.