Cbz-Pro-ψ[CH2SO2]-Cl | 212204-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Cbz-Pro-ψ[CH2SO2]-Cl
• 英文别名: Cbz-(S)-HPrs-Cl；Cbz-(S)-2-pyrrolidinemethanesulfonyl chloride；(S)-2-Chlorosulfonylmethyl-pyrrolidine-1-carboxylic acid benzyl ester；benzyl (2S)-2-(chlorosulfonylmethyl)pyrrolidine-1-carboxylate
• CAS: 212204-36-9
• 化学式: C₁₃H₁₆ClNO₄S
• 分子量: 317.793
• InChiKey: WFSXSKWRWQOOAY-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  Cbz-Pro-ψ[CH2SO2]-Cl 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 1,2-二氯乙烷 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-((((2S)-1-(N-benzoyl-L-alanyl)pyrrolidin-2-yl )methyl)-sulfonyl)-L-phenylalanine isopropylamide
  参考文献：
  名称：

  包含2-吡咯烷甲磺酸（2PyMS）残基的肽的构象行为†

  摘要：

  使用X射线，NMR和IR实验研究了含有2-吡咯烷甲磺酸（2PyMS）残基的模型肽的结晶状态和溶液中的构象行为。结果发现，在晶体中，二肽PhC（O）-2PyMS-Phe-NHiPr具有β-转构型，分子内氢键无法稳定该构型，可以归为IV型β-转型。在晶体状态下，三肽PhC（O）–翼–2PyMS–Phe–NHiPr以α-转角的形式存在，由2PyMS残基的吡咯烷氮原子形成的酰胺键具有不常见的顺式构象，到目前为止，在确定的紧密转弯中尚无紧密的类似物。尽管采用折叠构象的趋势仅部分保留在溶液中，但是2-PyMS可以被认为是设计具有非常规构象性质的折叠剂和拟肽的有前途的结构单元。

  DOI：

  10.1039/c2ob27058g
• 作为产物：
  描述：

  (S)-2-Acetylsulfanylmethyl-pyrrolidine-1-carboxylic acid benzyl ester 在 盐酸 、 N-氯代丁二酰亚胺 作用下， 以 水 、 乙腈 为溶剂， 生成 Cbz-Pro-ψ[CH2SO2]-Cl
  参考文献：
  名称：

  高效而简便的合成 ñ-Cbz-β-氨基链烷磺酰胺

  摘要：

  描述了一种合成N -Cbz-β-氨基链烷磺酰胺的有效方法。N -Cbz-β-氨基链烷磺酰胺很容易以高收率由多种氨基醇（包括旋光性氨基醇）制备，方法是用氯甲酸苄酯进行N -Cbz保护，用硫代乙酸进行Mitsunobu酯化反应，N-氯代琥珀酰亚胺氧化和氨解处理。

  DOI：

  10.1007/s11426-012-4607-9

文献信息

• Efficient synthesis of protected sulfonopeptides from N-protected 2-aminoalkyl xanthates and thioacetates
  作者：Saeed Kakaei、Jiaxi Xu

  DOI：10.1016/j.tet.2013.08.028

  日期：2013.10

  An efficient and convenient method was developed for the synthesis of protected sulfonopeptides via N-chlorosuccimide (NCS)/HCI oxidative chlorination of N-protected 2-aminoallcyl xanthates or thioacetates to the corresponding sulfonyl chlorides followed by aminolysis with amino esters. In the current method, sulfonopeptides containing 1- and 2-substituted taurines were prepared in satisfactory to good yields. It is a useful and efficient strategy for the synthesis of protected sulfonopeptides with functionalized side-chains. (C) 2013 Elsevier Ltd. All rights reserved.
• Investigation of a New Family of Chiral Ligands for Enantioselective Catalysis via Parallel Synthesis and High-Throughput Screening
  作者：Cesare Gennari、Simona Ceccarelli、Umberto Piarulli、Christian A. G. N. Montalbetti、Richard F. W. Jackson

  DOI：10.1021/jo980890p

  日期：1998.8.1
• Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2
  作者：Cesare Giordano、Anna Sansone、Annalisa Masi、Gino Lucente、Pasqualina Punzi、Adriano Mollica、Francesco Pinnen、Federica Feliciani、Ivana Cacciatore、Peg Davis

  DOI：10.1016/j.ejmech.2010.07.022

  日期：2010.10

  The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH(2); EM1 and Tyr-Pro-Phe-Phe-NH(2); EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH(2)) exhibit an extremely high selectivity for mu-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of beta-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3-pyrrolidinesulphonic acid (beta Prs) have been synthesized and their binding affinity and functional activity have been investigated. The highest p-receptor affinity is shown by [(S)beta Prs(2)]EM2 analogue (6e) which represents the first example of a beta-sulphonamido analogue in the field of mold peptides. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis and activity of fibrillogenesis peptide inhibitors related to the 17–21 β-amyloid sequence
  作者：Cesare Giordano、Annalisa Masi、Aldo Pizzini、Anna Sansone、Valerio Consalvi、Roberta Chiaraluce、Gino Lucente

  DOI：10.1016/j.ejmech.2008.03.036

  日期：2009.1

  Peptide derivatives 1-5, incorporating synthetic non-proteinogenic amino acids, related to the beta-amyloid 17-21 fragment of the amyloidogenic A beta(1-40), and the N-protected decapeptide 6, corresponding to a dimeric sequence of the same fragment, have been synthesized. These compounds were designed by using Soto's pentapeptide Ac-LPFFD-NH2 (iA beta 5p) as lead compound. Their activity as inhibitors of fibrillogenesis and stability against enzymatic degradation have been determined. Compounds 1, 5 and 6 are potent inhibitors in comparison to the lead compound. Exposure to chymotrypsin of peptide derivatives 1-5, all containing unnatural amino acids, shows increased stability as compared with iA beta 5p and 6. Conformational properties of the new compounds have been determined by CD and FF-IR spectroscopies. (C) 2008 Elsevier Masson SAS. All rights reserved.