Z-Asn-Phe-OMe | 4976-86-7

• 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: Z-Asn-Phe-OMe
• 英文别名: methyl (2S)-2-[[(2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoyl]amino]-3-phenylpropanoate
• CAS: 4976-86-7
• 化学式: C₂₂H₂₅N₃O₆
• 分子量: 427.457
• InChiKey: XHINWMJGDYTIFM-ROUUACIJSA-N

物化性质

• 熔点：
  193-194 °C
• 沸点：
  718.8±60.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-Asn-Phe-OMe 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 asparaginyl-phenylalanine methyl ester
  参考文献：
  名称：

  Structures, Sensory Activity, and Dose/Response Functions of 2,5-Diketopiperazines in Roasted Cocoa Nibs (Theobroma cacao)

  摘要：

  The taste compounds inducing the blood-like, metallic bitter taste sensation reported recently for a dichloromethane extract prepared from roasted cocoa nibs were identified as a series of 25 diketopiperazines by means of HPLC degustation, LC-MS/MS, and independent synthesis. Among these 25 compounds, 13 cis-configured diketopiperazines, namely, CYCIO(L-IIe-L-Phe), CYCIO(L-Val-L-Leu), CYCIO(L-Pro-L-Pro), CYCIO(L-IIe-L-Pro), CYCIO(L-Val-L-Tyr), CYCIO(L-Ala-L-Tyr), CYCIO(L-Phe-L-Ser), CYCIO(L-Ala-L-IIe), CYCIO(L-LeU-L-Phe), cyclo(L-Pro-L-Val), CYCIO(L-Pro-L-Thr), CYCIO(L-PrO-L-Tyr), and CYCIO(L-Val-L-Val) were identified for the first time in cocoa. In addition, the taste recognition thresholds for the metallic as well as the bitter taste of the diketopiperazines were determined, and after quantitative analysis by using two diastereomeric diketopiperazines as the internal standards, the sensory impact of the diketopiperazines was evaluated on the basis of their close-over-threshold (DoT) factors calculated as the ratio of the concentration and the threshold concentration of a compound. These data revealed DoT factors above 1.0 exclusively for cis-cyclo(L-Pro-L-Val), cis-cyclo(L-Val-L-Leu), cis-cyclo(L-Ala-L-IIe), cis-cyclo(L-Ala-L-Leu), and cis-cyclo(L-IIe-L-Pro), whereas all of the other diketopiperazines were present below their individual bitter taste threshold concentrations and should therefore not contribute to the cocoa taste. Because the DoT factors do not consider the nonlinear relationship between the concentration and gustatory response of an individual compound, we, for the first time, report on the recording of dose/response functions describing the human bitter taste perception of diketopiperazines more precisely.

  DOI：

  10.1021/jf051313m
• 作为产物：
  描述：

  N-苄氧羰基-L-天冬酰胺 、 L-苯丙氨酸甲酯盐酸盐 在 Sephadex G-50 、 三乙胺 、 bromelain 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 以90%的产率得到Z-Asn-Phe-OMe
  参考文献：
  名称：

  有机溶剂中菠萝蛋白酶催化合成多肽

  摘要：

  是一种来自菠萝茎提取物的硫醇蛋白酶。菠萝是台湾丰富的资源。菠萝蛋白酶（EC.3,4,4,24）是台湾出口的两种主要酶之一。这种酶的来源没有缺陷。因此，将菠萝蛋白酶应用于催化多肽合成具有巨大的潜力和经济价值。除在水溶液中催化聚合外，目前还没有利用菠萝蛋白酶合成多肽的研究成果。

  DOI：

  10.1002/jccs.200300025

文献信息

• A Novel Organophosphorus Compound as a Coupling Reagent for Peptide Synthesis
  作者：Chong-Xu Fan、Xiao-Lin Hao、Yun-Hua Ye

  DOI：10.1080/00397919608003508

  日期：1996.4

  Abstract 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4 (3H)-one 1 is a new organophosphorus compound which can be used as an efficient coupling reagent for peptide synthesis by either solution or solid phase coupling. Standard abbreviations for amino acids and protecting groups follow the IUPAC-IUB Joint Commission on Biochemistry Nomenclature: J. Biol. Chem. 1971, 247, 977.

  摘要 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4 (3H)-one 1 是一种新型有机磷化合物，可用作溶液偶联或固相偶联的肽合成的有效偶联剂。氨基酸和保护基团的标准缩写遵循 IUPAC-IUB 生物化学命名联合委员会：J. Biol。化学 1971、247、977。
• Amino Acids and Peptides. XI. Phosphorus in Organic Synthesis. VI. Application of Diphenyl Phosphorazidate to the Synthesis of Peptides containing Various Functions
  作者：TAKAYUKI SHIOIRI、SHUNICHI YAMADA

  DOI：10.1248/cpb.22.859

  日期：——

  Application of diphenyl phosphorazidate (DPPA) to the synthesis of peptides revealed that the DPPA method is quite general because it can be applied to the formation of peptides containing various functional groups. No difficulties were encountered when the side chains of serine, threonine, valine, glutamine, asparagine, methionine, histidine, tryptophan, and pyroglutamic acid were present in the carboxyl component. Arginine and cysteine showed no trouble when their side chain functions were protected with the nitro and benzyl groups, respectively. Serine, tyrosine, and histidine could be used as the amino component without any protection of the side chains. Fragment coupling of N-benzyloxycarbonylleucylleucine with valylphenylalanine methyl ester hydrochloride by DPPA showed that no racemization occurred.

  将磷酸二苯酯（DPPA）应用于多肽合成的结果表明，DPPA 方法具有很强的通用性，因为它可以用于合成含有各种官能团的多肽。当羧基成分中含有丝氨酸、苏氨酸、缬氨酸、谷氨酰胺、天冬酰胺、蛋氨酸、组氨酸、色氨酸和焦谷氨酸的侧链时，没有遇到任何困难。当精氨酸和半胱氨酸的侧链功能分别受到硝基和苄基的保护时，不会出现问题。丝氨酸、酪氨酸和组氨酸可用作氨基成分，无需对侧链进行任何保护。用 DPPA 将 N-苄氧羰基亮氨酸与戊基苯丙氨酸甲酯盐酸盐进行片段偶联，结果表明没有发生外消旋现象。
• Studies on Peptides. XLIII. Synthesis of Two Protected Peptides Related to the C-Terminal Portion of the Basic Trypsin Inhibitor from Bovine Pancreas (Kunitz and Northrop)
  作者：HARUAKI YAJIMA、YOSHIAKI KISO、KOUKI KITAGAWA

  DOI：10.1248/cpb.22.1079

  日期：——

  The protected nonadecapeptide and the C-terminal dipeptide corresponding to positions 38 through 56 and 57-58 of the basic trypsin inhibitor from bovine pancreas were prepared. Synthesis of the protected nonadecapeptide, Z (OMe)-Cys (Bzl)-Arg (Tos)-Ala-Lys (Z)-Arg (Tos)-Asn-Asn-Phe-Lys (Z)-Ser-Ala-Glu (OBzl)-Asp (OBzl)-Cys (Bzl)-Met-Arg (Tos)-Thr-Cys (Bzl)-Gly-OH, was achieved by condensation of three subunits : Z (OMe)-Cys (Bzl)-Arg (Tos)-Ala-Lys (Z)-Arg (Tos)-NHNH2 (positions 38-42), Z (OMe)-Asn-Asn-Phe-Lys (Z)-Ser-Ala-NHNH2 (positions 43-48) and Z (OMe)-Glu (OBzl)-Asp (OBzl)-Cys (Bzl)-Met-Arg (Tos)-Thr-Cys (Bzl)-Gly-OH (positions 49-56). The C-terminal dipeptide was prepared in a form of Z (OMe)-Gly-Ala-OH.

  制备了对应于来自牛胰腺的碱性胰蛋白酶抑制剂的38至56和57-58位的受保护的九肽和C端二肽。受保护的九肽 Z (OMe)-Cys (Bzl)-Arg (Tos)-Ala-Lys (Z)-Arg (Tos)-Asn-Asn-Phe-Lys (Z)-Ser-Ala-Glu 的合成（ OBzl)-Asp (OBzl)-Cys (Bzl)-Met-Arg (Tos)-Thr-Cys (Bzl)-Gly-OH，通过三个亚基缩合获得：Z (OMe)-Cys (Bzl)-Arg (Tos)-Ala-Lys (Z)-Arg (Tos)-NHNH2（位置 38-42），Z (OMe)-Asn-Asn-Phe-Lys (Z)-Ser-Ala-NHNH2（位置 43-48） )和Z(OMe)-Glu(OBzl)-Asp(OBzl)-Cys(Bzl)-Met-Arg(Tos)-Thr-Cys(Bzl)-Gly-OH(位置49-56)。 C端二肽以Z(OMe)-Gly-Ala-OH的形式制备。
• Serum thymic factor peptide analogs and process for the preparation
  申请人：SPOFA, spojene podniky pro zdravotnickouvyrobu

  公开号：US04711952A1

  公开（公告）日：1987-12-08

  Novel peptide analogs of the serum thymic factor are disclosed, structurally modified, in comparison with the natural substance, both in their N-terminal and C-terminal parts and inside the amino-acid sequence, corresponding to the general formula I A-Gly-Gly-Ser-Asn-B-C-NH-R (I), in which A is pGlu, Gln, Ala-Lys-Ser-Gln, pGlu-Ala-Lys-Ser-Gln or Gln-Ala-Lys-Ser-Gln, B and C are Gly, Phe, Leu, Ala or a direct bond, and R is H, an alkyl with 1 to 6 carbon atoms or a 2-phenylethyl. Depending upon their chemical structure, the subject thymic factor analogs possess either agonistic (immunostimulative) or antagonistic (immunosuppressory) properties.

  披露了血清胸腺因子的新型肽类似物，与天然物相比，在它们的N末端和C末端以及氨基酸序列内部进行了结构修改，对应于一般公式I A-Gly-Gly-Ser-Asn-B-C-NH-R（I），其中A为pGlu，Gln，Ala-Lys-Ser-Gln，pGlu-Ala-Lys-Ser-Gln或Gln-Ala-Lys-Ser-Gln，B和C为Gly，Phe，Leu，Ala或直接键，而R为H，具有1至6个碳原子的烷基或2-苯乙基。根据它们的化学结构，这些胸腺因子类似物具有激动性（免疫刺激）或拮抗性（免疫抑制）特性。
• Process for the preparation of alpha-L-aspartyl-L-phenylalanine alkyl esters
  申请人：FARCHEMIA S.p.A.

  公开号：EP0169937A2

  公开（公告）日：1986-02-05

  A process for the preparation of a-L-aspartyl-L-phenylalanine alkyl esters, and namely of the methyl ester or aspartame, characterized by using, as starting material, a L-asparagine derivative having the amino group protected, which is reacted with an alkyl ester of L-phenylalanine to produce a dipeptide whose amido group is subsequently converted to carboxylic group by means of nitrite ions.

  一种制备 a-L-天冬氨酰-L-苯丙氨酸烷基酯，即甲酯或阿斯巴甜的工艺，其特征是使用氨基受保护的 L-天冬氨酰胺衍生物作为起始原料，该衍生物与 L-苯丙氨酸烷基酯反应生成二肽，二肽的氨基随后通过亚硝酸离子转化为羧基。