4,4'-磺酰基二(2-氨基丁酸) | 31982-10-2

• 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: 4,4'-磺酰基二(2-氨基丁酸)
• 英文名称: L-homolanthionine
• 英文别名: L-Homolanthionine；(2S)-2-azaniumyl-4-[(3S)-3-azaniumyl-3-carboxylatopropyl]sulfanylbutanoate
• CAS: 31982-10-2
• 化学式: C₈H₁₆N₂O₄S
• 分子量: 236.292
• InChiKey: MBEPFGPQVBIIES-WDSKDSINSA-N

物化性质

• 熔点：
  269-272 °C (decomp)
• 沸点：
  499.5±45.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4,4'-磺酰基二(2-氨基丁酸) 、 三光气 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 以12%的产率得到
  参考文献：
  名称：

  含硫二氨基酸结构对共价交联共多肽水凝胶的影响

  摘要：

  生物产生的非规范二α-氨基酸以合理的收率和高纯度转化为新的二氮-羧基酸酐（di-NCA）单体。五个不同的二种NCA分别用共聚叔丁基-升-谷氨酸NCA，以获得能够形成具有变化的密度的交联剂水凝胶的共价交联共聚。比较水凝胶性质和残基结构，发现不同的二-α-氨基酸在交联形成中不相等。值得注意的是，升-cystine发现相比以产生显著弱凝胶升-homocystine，升-cystathionine，和升-lanthionine，表明升在制备共肽网络时，胱氨酸可能不是最佳的二α-氨基酸选择。二α-氨基酸交联剂还提供不同的化学稳定性，其中二硫键容易被还原降解，硫醚交联对还原稳定。这种响应差异可以提供一种手段来微调多肽生物材料网络的还原敏感性。

  DOI：

  10.1002/asia.201801031
• 作为产物：
  描述：

  S-benzyl-L-homocysteine 在 氨 、 sodium 作用下， 生成 4,4'-磺酰基二(2-氨基丁酸)
  参考文献：
  名称：

  The Preparation of the Diastereoisomers of Cystathionine and Homolanthionine¹

  摘要：

  DOI：

  10.1021/ja01150a026

文献信息

• Kanzaki, Hiroshi; Kobayashi, Michihiko; Nagasawa, Toru, Agricultural and Biological Chemistry, 1986, vol. 50, # 2, p. 391 - 398
  作者：Kanzaki, Hiroshi、Kobayashi, Michihiko、Nagasawa, Toru、Yamada, Hideaki

  DOI：——

  日期：——
• Design and synthesis of dimeric HIV-1 integrase inhibitory peptides
  作者：Krzysztof Krajewski、Ya-Qiu Long、Christophe Marchand、Yves Pommier、Peter P. Roller

  DOI：10.1016/s0960-894x(03)00679-6

  日期：2003.10

  Dimers of known HIV-1 integrase inhibitory hexapeptide H-His-Cys-Lys-Phe-Trp-Trp-NH2 containing different lengths of cross linkers in the place of cysteine residue, were designed, and synthesized. The inhibitory potency of these dimeric peptides is consistently higher than the lead hexapeptide. The dimeric peptide with djenkolic acid linker exhibited IC50 values of 5.3 and 6.5 muM, for 3'-end processing and strand transfer, respectively. (C) 2003 Elsevier Ltd. All rights reserved.
• H2S Biogenesis by Human Cystathionine γ-Lyase Leads to the Novel Sulfur Metabolites Lanthionine and Homolanthionine and Is Responsive to the Grade of Hyperhomocysteinemia
  作者：Taurai Chiku、Dominique Padovani、Weidong Zhu、Sangita Singh、Victor Vitvitsky、Ruma Banerjee

  DOI：10.1074/jbc.m808026200

  日期：2009.4

  Although there is a growing recognition of the significance of hydrogen sulfide (H2S) as a biological signaling molecule involved in vascular and nervous system functions, its biogenesis and regulation are poorly understood. It is widely assumed that desulfhydration of cysteine is the major source of H2S in mammals and is catalyzed by the transsulfuration pathway enzymes, cystathionine beta-synthase and cystathionine gamma-lyase (CSE). In this study, we demonstrate that the profligacy of human CSE results in a variety of reactions that generate H2S from cysteine and homocysteine. The gamma-replacement reaction, which condenses two molecules of homocysteine, yields H2S and a novel biomarker, homolanthionine, which has been reported in urine of homocystinuric patients, whereas a beta-replacement reaction, which condenses two molecules of cysteine, generates lanthionine. Kinetic simulations at physiologically relevant concentrations of cysteine and homocysteine, reveal that the alpha,beta-elimination of cysteine accounts for similar to 70% of H2S generation. However, the relative importance of homocysteine-derived H2S increases progressively with the grade of hyperhomocysteinemia, and under conditions of severely elevated homocysteine (200 mu M), the alpha,beta-elimination and gamma-replacement reactions of homocysteine together are predicted to account for similar to 90% of H2S generation by CSE. Excessive H2S production in hyperhomocysteinemia may contribute to the associated cardiovascular pathology.
• MICROORGANISM AND PROCESS FOR THE PREPARATION OF L-METHIONINE
  申请人：BASF SE

  公开号：EP1945043A2

  公开（公告）日：2008-07-23
• MONOTHIOETHER CROSSLINKERS IN POLYMERS AND APPLICATIONS THEREOF
  申请人：Zymergen Inc.

  公开号：US20210206802A1

  公开（公告）日：2021-07-08

  A polypeptide comprises amino acids in an amino acid sequence, wherein a portion of the amino acids are covalently linked via a monothioether bridge. In one embodiment, the portion includes amino acids selected from (I) herein n is 0, 1, or 2 and m is 1 or 2. In another embodiments, a hydrogel can include such an amino acid as a crosslinker.