S-(9H-xanthen-9-yl)cysteine | 73044-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: S-(9H-xanthen-9-yl)cysteine
• 英文别名: S-(9H-xanthen-9-yl)-L-cysteine；S-xanthen-9-yl-L-cysteine；S-Xanthen-9-yl-L-cystein；(2R)-2-amino-3-(9H-xanthen-9-ylsulfanyl)propanoic acid
• CAS: 73044-60-7
• 化学式: C₁₆H₁₅NO₃S
• 分子量: 301.366
• InChiKey: MBHPYNPNSDDOSI-LBPRGKRZSA-N

物化性质

• 沸点：
  492.1±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-(9H-xanthen-9-yl)cysteine 、 三苯基氯甲烷 在 二乙胺 作用下， 以 氯仿 、 水 为溶剂， 以72%的产率得到N^α-trityl-S-(9H-xanthen-9-yl)-L-cysteine
  参考文献：
  名称：

  在树脂上合成的天然化学连接的环肽1 ，2

  摘要：

  一种新的半胱氨酸衍生物，Ñ α三苯甲基小号- （9 ħ -呫吨-9-基） -升-半胱氨酸[TRT-半胱氨酸（克桑）-OH]已引入用于肽合成的，专门为应用到一个新的战略用于制备环肽。进行以下步骤以合成环状模型肽环（Cys-Thr-Abu-Gly-Gly-Ala-Arg-Pro-Asp-Phe）：（i）Fmoc-Asp-OAl通过其侧链锚定将β-羧基作为对烷氧基苄基酯游离到固体载体上；（ii）通过标准Fmoc / t逐步提高肽链的延伸率Bu固相化学；（iii）除去N-末端的Fmoc基团；（iv）Trt-Cys（Xan）-OH的偶联；（v）C末端烯丙基酯的选择性Pd（0）促进的裂解；（vi）预活化为硫酯的C-末端残基，即H-Phe-SBzl的偶联；（ⅶ）选择性移除的Ñ α -Trt和小号-Xan保护基团非常温和的酸性条件下; （viii）在水性环境中通过天然化学连接在树脂上进行环化；（ix）从树

  DOI：

  10.1021/jo049839d
• 作为产物：
  描述：

  占吨醇 、 L-半胱氨酸盐酸盐无水物 在 溶剂黄146 作用下， 生成 S-(9H-xanthen-9-yl)cysteine
  参考文献：
  名称：

  Dickman; Westcott, Journal of Biological Chemistry, 1954, vol. 210, p. 481,483

  摘要：

  DOI：

文献信息

• Multi-valent guanidinium compounds for enhancing molecular translocation across cellular membranes and epithelial tissues
  申请人：Hou Zheng

  公开号：US20070078078A1

  公开（公告）日：2007-04-05

  Disclosed herein are guanidinium containing compounds consisting of a core moiety with a plurality of side chains containing guanidinium groups. Such compounds have enhanced translocation across cellular membranes and epithelial tissues. The compounds may also have a therapeutic or other biologically active moiety attached so that these moieties may be effectively transported into a cell by the guanidinium containing compound.

  本文披露了含有胍基的化合物，其由具有多个含有胍基的侧链的核心部分组成。这些化合物具有穿过细胞膜和上皮组织的增强转运能力。这些化合物也可以附着有治疗或其他生物活性基团，以便这些基团可以通过含有胍基的化合物有效地转运到细胞内。
• Novel <i>S</i>-Xanthenyl Protecting Groups for Cysteine and Their Applications for the <i>N</i>^α-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis^1-3
  作者：Yongxin Han、George Barany

  DOI：10.1021/jo961882g

  日期：1997.6.13

  The 9H-xanthen-9-yl (Xan) and 2-methoxy-9H-xanthen-9-yl (2-Moxan) groups can be introduced onto sulfhydryl functions by S-alkylation reactions involving the corresponding xanthydrols, plus trifluoroacetic acid (TFA) as catalyst. Conversely, these groups are removed rapidly by acid in the presence of appropriate silane or thiol scavengers. The 3-methoxy-9H-xanthen-9-yl (3-Moxan) derivative was also studied, but abandoned for several reasons including challenging synthesis, excessive lability to acid, and insufficient stability in the presence of base. The N-alpha-9-fluorenyl-methyloxycarbonyl (Fmoc), S-Xan or 2-Moxan-protected cysteine derivatives were prepared and applied to the solid-phase syntheses of several model peptides. Selective removal of S-Xan and S-2-Moxan groups, while retaining tris(alkoxybenzyl)amide (PAL) anchoring, is best accomplished with TFA-CH2Cl2-Et3SiH (1:98.5:0.5), 25 degrees C, 2 h. Alternatively, oxidative deprotection of S-Xan or S-2-Moxan with iodine (10-20 equiv) or thallium(III) tris(trifluoroacetate) [Tl(tfa)(3)] (1-3 equiv) to provide disulfides can be carried out on peptide substrates both in solution and while polymer-bound. Compared to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (Trt) group, S-Xan and S-2-Moxan gave equal or superior results in terms of peptide purities (including no detectable tryptophan alkylation) and overall yields.
• US4267344A
  申请人：——

  公开号：US4267344A

  公开（公告）日：1981-05-12
• US7745392B2
  申请人：——

  公开号：US7745392B2

  公开（公告）日：2010-06-29
• [EN] MULTI-VALENT GUANIDINIUM COMPOUNDS FOR ENHANCING MOLECULAR TRANSLOCATION ACROSS CELLULAR MEMBRANES AND EPITHELIAL TISSUES<br/>[FR] COMPOSES GUANIDINIUM MULTIVALENTS PERMETTANT D'AUGMENTER LA TRANSLOCATION MOLECULAIRE A TRAVERS DES MEMBRANES CELLULAIRES ET DES TISSUS EPITHELIAUX
  申请人：NITTO DENKO CORP

  公开号：WO2007038169A2

  公开（公告）日：2007-04-05

  [EN] Disclosed herein are guanidinium containing compounds consisting of a core moiety with a plurality of side chains containing guanidinium groups. Such compounds have enhanced translocation across cellular membranes and epithelial tissues. The compounds may also have a therapeutic or other biologically active moiety attached so that these moieties may be effectively transported into a cell by the guanidinium containing compound.
  [FR] L'invention concerne des composés contenant du guanidinium qui comprennent un fragment central présentant une pluralité de chaînes latérales contenant des groupes guanidinium. Lesdits composés permettent d'augmenter la translocation à travers des membranes cellulaires et des tissus épithéliaux. Un fragment thérapeutique ou un autre fragment actif sur le plan biologique est également lié auxdits composés de façon que les fragments soient transportés efficacement dans une cellule par le composé contenant du guanidinium.