L-N-acetyl-3-(4-(chloromethyl)phenyl)alanine ethyl ester | 130887-73-9

• 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: L-N-acetyl-3-(4-(chloromethyl)phenyl)alanine ethyl ester
• 英文别名: N-Ac-L-Phe(p-CH2Cl).OEt；Ac-L-Phe(p-CH2Cl)-OEt；Ac-L-Phe(4-CH2Cl)-OEt；N-Acetyl-4-(chloromethyl)-L-phenylalanine ethyl ester；ethyl (2S)-2-acetamido-3-[4-(chloromethyl)phenyl]propanoate
• CAS: 130887-73-9
• 化学式: C₁₄H₁₈ClNO₃
• 分子量: 283.755
• InChiKey: CIAQWTMEOZOLIA-ZDUSSCGKSA-N

物化性质

• 沸点：
  459.2±40.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-N-acetyl-3-(4-(chloromethyl)phenyl)alanine ethyl ester 在 盐酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 21.0h， 生成 FMOC-L-4-磷酸基苯丙氨酸
  参考文献：
  名称：

  An Efficient Synthesis of N^α-Fmocm-(phosphonomethyl)-L- and D-Phenylalanine

  摘要：

  DOI：

  10.1080/00397919908086231
• 作为产物：
  描述：

  N-乙酰-L-苯丙氨酸乙酯 、 氯甲基甲基醚 在 zinc(II) chloride 作用下， 反应 8.0h， 以70%的产率得到L-N-acetyl-3-(4-(chloromethyl)phenyl)alanine ethyl ester
  参考文献：
  名称：

  An Efficient Synthesis of N^α-Fmocm-(phosphonomethyl)-L- and D-Phenylalanine

  摘要：

  DOI：

  10.1080/00397919908086231

文献信息

• Enantioselective Synthesis of Protected <scp>l</scp>-4-[Sulfonamido(difluoromethyl)]phenylalanine and <scp>l</scp>-4-[Sulfonamido(methyl)]phenylalanine and an Examination of Hexa- and Tripeptide Platforms for Evaluating pTyr Mimics for PTP1B Inhibition
  作者：Bryan Hill、Vanessa Ahmed、Daniel Bates、Scott D. Taylor

  DOI：10.1021/jo061496r

  日期：2006.10.1

  These amino acids were incorporated into two peptide sequences, DADE-X-LNH2 and FmocGlu(OBn)-X-LNH2, which have previously been employed as platforms for assessing pTyr mimics for inhibition of protein tyrosine phosphatase 1B (PTP1B). Inhibition studies with these and other peptides and PTP1B revealed that good inhibition could be obtained using the tripeptide platform, although the presence of a pTyr

  的第一对映选择性合成升-4-（sulfonamidomethyl）苯丙氨酸和升- [亚磺酰氨基（二氟甲基）]苯丙氨酸肽合成适当保护的描述。合成1-（磺酰胺基甲基）苯丙氨酸的关键步骤是在Ac - 1 -Phe（4-CH 2 SCOCH 3）-OEt上进行氧化氯化，得到粗制的Ac - 1 -Phe（4-CH 2 SO 2 Cl） -OEt，它可以与胺反应得到相应的磺酰胺。l准备的关键-[磺酰胺基（二氟甲基）]苯丙氨酸是高度对映选择性的反应，涉及威廉的助剂和苄基溴化物中间体。这些氨基酸被并入两个肽序列DADE-X-LNH 2和FmocGlu（OBn）-X-LNH 2，它们先前已用作评估pTyr模拟物对蛋白酪氨酸磷酸酶1B（PTP1B）抑制的平台。用这些肽和其他肽以及PTP1B进行的抑制研究表明，使用三肽平台可以获得良好的抑制作用，尽管良好抑制并不需要pTyr模拟物的存在。这些结果表明FmocGlu（OBn）-X-LNH
• Synthesis of human CCK26-33 and CCK-33 related analogs on 2,4-DMBHA and TMBHA
  作者：Maria Teresa Machini Miranda、Rodger A. Liddle、Jean E. Rivier

  DOI：10.1021/jm00064a001

  日期：1993.6

  New analogues of human cholecystokinin in which the Tyr(SO3H) has been replaced by Phe(p-CH2SO3Na), methionines by norleucines, and tryptophan by 2-naphthylalanine[Phe(p-CH2-SO3Na)27,Nle28,31,Nal30]-CCK26-33 and [Phe(p-CH2SO3Na)27,Nle7,28,31,Nal30]-CCK-331 were synthesized by Fmoc solid phase methodology on two different resins (2,4-dimethoxybenzhydrylamine- and 4-(benzyloxy)-2',4'-dimethoxybenzhydrylamine resins, 2,4-DMBHA and TMBHA resins, respectively). While the syntheses on the TMBHA appeared to be more sluggish than those carried out on the 2,4-DMBHA, both final crude products were of equivalent relative purity and after purification gave approximately the same final yields of analogues estimated to have a purity greater than 93 % using RPHPLC and CZE. The peptides were further characterized by amino acid analysis and LSIMS. Phe(p-CH2SO3Na)27,Nle7,28,31,Nal30]-CCK-33 was submitted to 33 Edman cycles and shown to be the desired product with less than 3 % preview. Both analogues were tested for their ability to stimulate amylase release from isolated rat pancreatic acini. In this assay, [Phe(p-CH2SO3Na)27,Nle28,31,Nal30] -CCK26-33 and Phe(p-CH2SO3Na)27,Nle7,28,31,Nal30]-CCK-33 were 10 and 30 times less potent than CCK-8, respectively.
• LIU, KELIANG;HE, BINGLIN;XIAO, SHAOBO, INYUN XUASYUEH, 7,(1990) N, S. 72-74
  作者：LIU, KELIANG、HE, BINGLIN、XIAO, SHAOBO

  DOI：——

  日期：——
• [EN] PEPTIDES AND COMPOUNDS THAT BIND TO SH2 DOMAINS<br/>[FR] PEPTIDES ET COMPOSES SE FIXANT AUX DOMAINES SH2
  申请人：AFFYMAX TECHNOLOGIES N.V.

  公开号：WO1996023813A1

  公开（公告）日：1996-08-08

  (EN) The present invention generally relates to peptides and compounds which bind to the SH2 domain or domains of various proteins, as well as methods for identifying such peptides and compounds. These peptides and compounds have application as agonists and antagonists of SH2 domain containing proteins, and as diagnostic or therapeutic agents for the diagnosis or treatment of disease conditions.(FR) Cette invention traite, d'une manière générale, de peptides et de composés se fixant au domaine SH2 ou à des domaines de diverses protéines, ainsi que de procédés permettant d'identifier ces peptides et composés. Ceux-ci sont utilisés comme agonistes et antagonistes du domaine SH2 contenant des protéines et comme agents diagnostiques et thérapeutiques pour le diagnostic ou le traitement d'états pathologiques.
• An Efficient Synthesis of N^α-Fmocm-(phosphonomethyl)-L- and D-Phenylalanine
  作者：Liu Bo、Zhan Jiarong

  DOI：10.1080/00397919908086231

  日期：1999.7