(2S,5R)-(+)-hydroxylysine dihydrochloride | 93923-90-1

• 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
• 英文名称: (2S,5R)-(+)-hydroxylysine dihydrochloride
• 英文别名: (2S,5R)-2,6-bis(azaniumyl)-5-hydroxyhexanoate;chloride
• CAS: 93923-90-1
• 化学式: C₆H₁₄N₂O₃*2ClH
• 分子量: 235.111
• InChiKey: MJXVOTKVFFAZQJ-JBUOLDKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.21
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5R)-(+)-hydroxylysine dihydrochloride 在 sodium hydroxide 、 三氟化硼乙醚 、 sodium carbonate 、 copper(II) sulfate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 81.5h， 生成 (2S,5R)-Fmoc-2-amino-4-(3-Boc-2,2-dimethyl-oxazolidin-5-yl)-butyric acid
  参考文献：
  名称：

  掩蔽的侧链醛氨基酸，用于固相合成和连接

  摘要：

  掩蔽的醛氨基酸Fmoc-Hyl（Boc-恶唑烷）1已通过五个步骤（3个罐）由母体氨基酸合成。所采用的保护方案使1非常适合于标准的基于Fmoc的肽和类似结构的固相组装，包括基于TFA的脱保护。所得的肽具有侧链1,2-氨基醇，并且在TFA处理后，未保护的肽的高碘酸盐氧化掩盖了醛的功能。给定的转化顺序可以避免已知的，有问题的醛在TFA溶液中的释放。TFA后产生的肽醛已用于模型化学选择性连接中，并形成了construct构建物。此外，Fmoc-Hyl（Alloc-oxazolidine）10 合成后，用于树脂上醛的产生和的转化

  DOI：

  10.1016/s0040-4039(02)00230-7
• 作为产物：
  描述：

  (S)-6-oxo-N-(tert-butyloxycarbonyl)-pipecolic acid tert-butyl ester 在 10percent Pd/C 2,3,5-三甲基吡啶 、 盐酸 、 sodium tetrahydroborate 、 sodium azide 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.5h， 生成 (2S,5R)-(+)-hydroxylysine dihydrochloride
  参考文献：
  名称：

  Diastereoselective Hydroxylation of 6-Substituted Piperidin-2-ones. An Efficient Synthesis of (2S,5R)-5-Hydroxylysine and Related α-Amino Acids

  摘要：

  The synthesis of (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylates (5) and related (3S,W-3hydroxy-6-alkyl-2-oxo-1-piperidinecarboxylates has been developed. The approach is based on the asymmetric hydroxylation of enolates generated from the corresponding N-protected-6-substituted piperidin-2-ones. The utility of 5a as a precursor in the synthesis of (2S,5R)-5-hydroxylysine (1), an amino acid unique to collagen and collagen-like proteins, has also been demonstrated. (2S)-6oxo-1,2-piperidinedicarboxylates (6) required for hydroxylation studies were prepared in 38-74% yield, starting from conveniently protected aspartic acid as inexpensive chiral adduct. Hydroxylation of 6 to 5 proceeds in high yield and excellent diastereoselectivity by treatment of their Li-enolate with (+)-camphorsulfonyloxaziridine at -78 degreesC. Ring opening of di-tert-butyl (2S,5R)-6-oxo-1,2-piperidinedicarboxylate ((5R)-5a) under reductive conditions afforded the corresponding 1,2-diol (17) in 91%, which was further transformed to (2S,5R)-5-hydroxylysine in four steps (84%). 17 is also a versatile intermediate in the preparation of tert-butyl (2S,M)-2-[(tert-butoxycarbonyl)aminol 5-hydroxy-6-iodohexanoate (3) and tert-butyl (2S)-2-[(tert-butoxycarbonyl)aminol-4-[(2,R)-oxiranyl]- butanoate (4), two amino acid derivatives used in the total synthesis of the bone collagen cross-link (+)-pyridinoline (2a).

  DOI：

  10.1021/jo025950c

文献信息

• Syntheses of structurally diverse amino acids, including δ-hydroxylysine, using the acyl nitroso Diels–Alder reaction
  作者：Lee Bollans、John Bacsa、Daniel A. O’Farrell、Scott Waterson、Andrew V. Stachulski

  DOI：10.1016/j.tetlet.2010.02.076

  日期：2010.4

  with fully controlled relative stereochemistry, the acyl nitroso Diels–Alder (ANDA) reaction is ideally suited to the synthesis of structurally diverse, including hydroxylated, amino acids. The major issue to be tackled is that of regiochemistry in the ANDA addition to unsymmetrical dienes. The transformation of three diverse types of ANDA adducts into amino acids is described, in particular, the synthesis

  借助亚硝基Diels-Alder（ANDA）反应，它可以在完全受控的相对立体化学条件下以1,4-关系引入氨基和羟基官能团，因此非常适合合成结构多样的氨基酸，包括羟基化的氨基酸。要解决的主要问题是除不对称二烯外的ANDA中的区域化学问题。描述了三种不同类型的ANDA加合物向氨基酸的转化，特别是作为保护形式的单一（2 SR，5 SR）非对映异构体，δ-羟基赖氨酸（胶原的重要组成部分）的合成。
• An Expedient Synthesis of LAF389, a Bengamide B Analogue
  作者：David D. Xu、Liladhar Waykole、John V. Calienni、Lech Ciszewski、George T. Lee、Wenming Liu、Joanna Szewczyk、Kevin Vargas、Kapa Prasad、Oljan Repič、Thomas J. Blacklock

  DOI：10.1021/op0341162

  日期：2003.11.1

  convergent, safe synthesis of LAF389 (9), an anti-cancer agent analogous to bengamide B, is described. Starting from α-d-glucoheptonic (d-glycero-d-gulo-heptonic acid) γ-lactone (10), the lactone 15 was constructed in five steps. Major improvements were made in the preparation of the aldehyde precursor 14 and subsequent olefination to yield 15 via a modified Julia protocol. This olefination was significantly

  描述了 LAF389 (9) 的优化、收敛、安全合成，这是一种类似于苯甲酰胺 B 的抗癌剂。从α-d-葡庚糖（d-甘油-d-古洛庚酸）γ-内酯（10）开始，分五步构建内酯15。在醛前体 14 的制备和随后的烯烃化以通过改进的 Julia 方案产生 15 方面进行了重大改进。通过使用 TMSCl 作为添加剂，这种烯烃化得到了显着改善。药物物质的第二个片段，ε-己内酰胺 7，是从 (5R)-5-羟基-l-赖氨酸 (1) 中通过两次一锅法获得的。最后，使用 2-乙基己酸钠 (Na-EH) 用 7 打开 15，得到 8，其脱保护得到 LAF389。
• Chemical Synthesis of Ubiquitin, Ubiquitin-Based Probes, and Diubiquitin
  作者：Farid El Oualid、Remco Merkx、Reggy Ekkebus、Dharjath S. Hameed、Judith J. Smit、Annemieke de Jong、Henk Hilkmann、Titia K. Sixma、Huib Ovaa

  DOI：10.1002/anie.201005995

  日期：2010.12.27

  Changing the subject: An efficient linear solid‐phase peptide synthesis of ubiquitin (Ub) has been developed. This approach allows the incorporation of desired tags and mutations (see picture; blue denotes a pseudoproline dipeptide, red a dimethoxybenzyl dipeptide) as well as specific C‐terminal modification and the construction of all diubiquitin conjugates in high yields and purities in a straightforward

  改变话题：一种有效的泛素（Ub）线性固相肽合成方法已被开发出来。这种方法允许掺入所需的标签和突变（见图；蓝色表示假脯氨酸二肽，红色表示二甲氧基苄基二肽）以及特定的 C 末端修饰，并以简单的方式以高产量和纯度构建所有双泛素缀合物。
• Synthesis of immunoreagents for measurement of galactosylhydroxylysine
  作者：Maciej Adamczyk、Rajarathnam E. Reddy

  DOI：10.1016/s0957-4166(99)00331-6

  日期：1999.8

  (2S,5R)-(+)-Hydroxylysine (6) was transformed into (-)-succinimidyl ester (13) and conjugated to BSA or KLH to form immunogens (2 and 3) for generation of anti-galactosylhydroxylysine antibodies. Additionally, treatment of (-)-13 with 6-Fln-CH2NH2 (16) or acridinium derivative (17) and subsequent hydrolysis gave the fluorescent (4) and chemiluminescent (5) tracers, respectively. These immunoreagents (3,4 and 5,6) are essential for development of assays for diagnosis of osteoporosis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (2S,5R)-(+)-羟基赖氨酸(6)被转化为(-)-琥珀酰亚胺酯(13)，并通过与BSA或KLH结合形成免疫原(2和3)，用于生成抗半乳糖基羟基赖氨酸抗体。此外，将(-)-13分别与6-Fln-CH2NH2(16)或吖啶衍生物(17)处理后再进行水解，分别得到荧光示踪剂(4)和化学发光示踪剂(5)。这些免疫试剂(3、4和5、6)对于开发诊断骨质疏松症的检测方法至关重要。©1999 Elsevier Science Ltd. 保留所有权利。
• Punch and die
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1164002A2

  公开（公告）日：2001-12-19

  An object of the present invention is to provide a punch or die having excellent corrosion resistance and releasing property which is suitable for a tablet machine particularly for the production of tablets containing corrosive substance(s) and adhesive substance(s). Thus, the present invention relates to a punch or die for compressing granules to prepare tablets, where a high-silicon steel is used as a basis material.

  本发明的目的是提供一种冲头或模具，它具有优异的耐腐蚀性和脱模性，适用于片剂机，特别是用于生产含有腐蚀性物质和粘性物质的片剂。因此，本发明涉及一种用于压缩颗粒以制备片剂的冲头或模具，其中使用高硅钢作为基础材料。