L-asparagine benzyl ester trifluoroacetate | 105220-22-2

• 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
• 英文名称: L-asparagine benzyl ester trifluoroacetate
• 英文别名: H-Asn-OBzl, TFA；H-Asn-OBzl*TFA；H-Asn-OBn*TFA；[(2S)-4-amino-1,4-dioxo-1-phenylmethoxybutan-2-yl]azanium;2,2,2-trifluoroacetate
• CAS: 105220-22-2
• 化学式: C₂HF₃O₂*C₁₁H₁₄N₂O₃
• 分子量: 336.268
• InChiKey: PYVGEIMKGFEYGL-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.49
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  肉豆蔻酸 、 L-asparagine benzyl ester trifluoroacetate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以23%的产率得到
  参考文献：
  名称：

  从pks岛中分离出代谢物，可深入了解Colibactin的生物合成和活性

  摘要：

  Colibactin是由共生和致病菌株产生结构上未表征的，基因毒性的天然产物的大肠杆菌窝藏的PKS岛。从pks +大肠杆菌突变体中分离出一种新的代谢物，该突变体缺少必不可少的生物合成酶。该分子的不寻常的azaspiro [2.4]双环系统为大肠菌素的生物合成提供了新的见识，并提出了大肠菌素和其他pks衍生代谢物可能通过其产生遗传毒性的机制。

  DOI：

  10.1021/acs.orglett.5b00432
• 作为产物：
  描述：

  溴甲苯 在 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 L-asparagine benzyl ester trifluoroacetate
  参考文献：
  名称：

  校正从pks岛中分离出的代谢物可提供对Colibactin生物合成和活性的见解

  摘要：

  经修订的文件，其中包含对表S3中化学位移的更正。该材料可通过互联网（http://pubs.acs.org）免费获得。这篇文章被3个出版物引用。经修订的文件，其中包含对表S3中化学位移的更正。该材料可通过互联网（http://pubs.acs.org）免费获得。

  DOI：

  10.1021/acs.orglett.5b01056

文献信息

• Structure-activity relationships of C-terminal tri- and tetrapeptide fragments that inhibit gastrin activity
  作者：Jean Martinez、Jean Pierre Bali、Richard Magous、Janine Laur、Marie Francoise Lignon、Christian Briet、Dino Nisato、Bertrand Castro

  DOI：10.1021/jm00381a002

  日期：1985.3

  A series of tri- and tetrapeptide derivatives, analogues of the gastrin C-terminal region with no phenylalanine residue, were synthesized. These peptides were tested for their ability to inhibit gastrin-stimulated acid secretion in vivo as well as binding of [125I]-(Nle11)-HG-13 to gastric mucosal cell receptors in vitro. Most of the peptides tested exhibited gastrin antagonist activity in vivo and in vitro. Most active derivatives were 20-30 times more potent than the well-known gastrin antagonist derivatives proglumide and benzotript and had 20-200 times more binding affinity. The smallest fragment exhibiting antagonist activity was the tripeptide Boc-L-tryptophyl-L-methionyl-L-aspartic acid amide.
• Amino Acids and Peptides. XXXIII. Synthesis of N-Terminal Epitope Peptides of Mammalian Metallothioneins(MTs).
  作者：Yoshio OKADA、Shigeru NAKAYAMA、Shin IGUCHI、Yutaka KIKUCHI、Masachika IRIE、Jun-ichi SAWADA、Hideharu IKEBUCHI、Tadao TERAO

  DOI：10.1248/cpb.40.1029

  日期：——

  In order to determine the fine structure of the mammalian metallothionein (MT) epitope to a monoclonal anti-rat Zn-MT-II antibody (MT 189-14-7), N-terminal peptides of various lengths of mammalian metallothioneins (MTs) were synthesized by a conventional solution method using the newly developed beta-2-adamantylaspartate, and their immunological properties were examined. It was found that the N-terminal acetyl group was indispensable for the reaction with the monoclonal antibody and the N-terminally acetylated pentapeptide, Ac-Met-Asp-Pro-Asn-Cys-OH, was the smallest peptide which exhibited a significant reactivity with the antibody.
• Diaz, Joseph; Guegan, Remy; Muneaux, Yvette, Bulletin de la Societe Chimique de France, 1989, # 4, p. 493 - 510
  作者：Diaz, Joseph、Guegan, Remy、Muneaux, Yvette、Perreaut, Pierre、Vedel, Michel、et al.

  DOI：——

  日期：——
• Total Synthesis of TMC-95A
  作者：Masayuki Inoue、Hayato Sakazaki、Hidetomo Furuyama、Masahiro Hirama

  DOI：10.1002/anie.200351130

  日期：2003.6.16
• Isolation of a Metabolite from the <i>pks</i> Island Provides Insights into Colibactin Biosynthesis and Activity
  作者：Carolyn A. Brotherton、Matthew Wilson、Gary Byrd、Emily P. Balskus

  DOI：10.1021/acs.orglett.5b00432

  日期：2015.3.20

  Colibactin is a structurally uncharacterized, genotoxic natural product produced by commensal and pathogenic strains of E. coli that harbor the pks island. A new metabolite has been isolated from a pks+E. coli mutant missing an essential biosynthetic enzyme. The unusual azaspiro[2.4] bicyclic ring system of this molecule provides new insights into colibactin biosynthesis and suggests a mechanism through

  Colibactin是由共生和致病菌株产生结构上未表征的，基因毒性的天然产物的大肠杆菌窝藏的PKS岛。从pks +大肠杆菌突变体中分离出一种新的代谢物，该突变体缺少必不可少的生物合成酶。该分子的不寻常的azaspiro [2.4]双环系统为大肠菌素的生物合成提供了新的见识，并提出了大肠菌素和其他pks衍生代谢物可能通过其产生遗传毒性的机制。