H-Ser-Ala-OMe | 45083-43-0

• 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: H-Ser-Ala-OMe
• 英文别名: (S)-2-((S)-2-amino-3-hydroxypropionylamino)propionic acid methyl ester；Ser-Ala-OMe；methyl (2S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]propanoate
• CAS: 45083-43-0
• 化学式: C₇H₁₄N₂O₄
• 分子量: 190.199
• InChiKey: VGRRCGOKYUBRQO-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-Ser-Ala-OMe 在 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 Z-Leu-Ser-Ala-N2H3
  参考文献：
  名称：

  Synthesis of PHI (peptide histidine isoleucine) and related peptides and immunochemical confirmation of amino acid residue in position 24 of PHI with use of the synthetic peptides

  摘要：

  DOI：

  10.1021/ja00337a046
• 作为产物：
  描述：

  Z-Ser-Ala-OMe 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、3.45 MPa 条件下， 反应 48.0h， 生成 H-Ser-Ala-OMe
  参考文献：
  名称：

  Impact of Dehydroamino Acids on the Structure and Stability of Incipient 3₁₀-Helical Peptides

  摘要：

  A comparative study of the impact of small, medium-sized, and bulky alpha,beta-dehydroamino acids (Delta AAs) on the structure and stability of Balarams incipient 3(10)-helical peptide (1) is reported. Replacement of the N-terminal Aib residue of 1 with a Delta AA afforded peptides 2a-c that maintained the 3(10)-helical shape of 1. In contrast, installation of a Delta AA in place of Aib-3 yielded peptides 3a-c that preferred a beta-sheet-like conformation. The impact of the Delta AA on peptide structure was independent of size, with small (Delta Ala), medium-sized (Z-Delta Abu), and bulky (Delta Val) Delta AAs exerting similar effects. The proteolytic stabilities of 1 and its analogs were determined by incubation with Pronase. Z-Delta Abu and Delta Val increased the resistance of peptides to proteolysis when incorporated at the 3-position and had negligible impact on stability when placed at the 1-position, whereas Delta Ala-containing peptides degraded rapidly regardless of position. Exposure of peptides 2a-c and 3a-c to the reactive thiol cysteamine revealed that Delta Ala-containing peptides underwent conjugate addition at room temperature, while Z-Delta Abu- and Delta Val-containing peptides were inert even at elevated temperatures. These results suggest that both bulky and more accessible medium-sized Delta AAs should be valuable tools for bestowing rigidity and proteolytic stability on bioactive peptides.

  DOI：

  10.1021/acs.joc.9b02747

文献信息

• Indium mediated allylation in peptide and protein functionalization
  作者：Jenefer Alam、Thomas H. Keller、Teck-Peng Loh

  DOI：10.1039/c1cc12926k

  日期：——

  Indium-mediated allylation has been used in the site-selective functionalization of N-terminal aldehydes of peptides and proteins. This is the first demonstration of indium-mediated C–C bond formation in protein labelling studies under mild and environmentally friendly conditions.

  铟介导的烯丙基化反应已被用于肽和蛋白质N端醛基的位点选择性功能化。这是在温和且环境友好的条件下，首次展示铟介导的C-C键形成在蛋白质标记研究中的应用。
• Synthesis of hpGRF(Somatocrinin) in liquid phase and intermediate
  申请人：Sanofi

  公开号：US04704450A1

  公开（公告）日：1987-11-03

  The invention relates to synthesis of hpGRF (Somatocrinin) in liquid phase and to intermediate peptides, comprising: coupling, one after the other and in the order of the sequence of the GRF, the fragments in which: (a) the side acid functions of the aspartic and glutamic acids and the side amine function of the lysine are protected by protector groups stable in the conditions of deprotection of the group Boc, (b) the guanidine function of the arginine is protected by protonation, and (c) the N-terminal amino acid is protected on the amine by the Boc group; selectively eliminating the group Boc from the N-terminal amine of the peptide in phase of elongation by hydrolysis with trifluoroacetic acid, said coupling being effected in an aprotic polar solvent and eliminating, at the end of sequence, all the protector groups by hydrolysis with the aid of a 0.1 to 1M solution of methanesulfonic or trifluoromethanesulfonic acid in trifluoroacetic acid.

  本发明涉及在液相中合成hpGRF（生长激素释放肽）以及包括以下中间肽段的方法：按照GRF序列的顺序，依次耦合各片段，其中：（a）通过稳定的保护基保护天冬氨酸和谷氨酸的侧链酸性功能以及赖氨酸的侧链胺基功能，以防止在去除Boc基团的条件下发生脱保护反应；（b）通过质子化来保护精氨酸的胍基功能；（c）通过Boc基团在氨基上保护N-末端氨基酸。在伸长相的肽段中，通过三氟乙酸水解选择性地消除肽段N-末端氨基上的Boc基团。该耦合在无水极性溶剂中进行，最终在序列结束时，通过在三氟乙酸中使用0.1至1M的甲烷磺酸或三氟甲磺酸溶液水解去除所有保护基。
• Synthesis of hGRF (somatocrinin) in liquid phase and intermediate
  申请人：Sanofi

  公开号：US04707541A1

  公开（公告）日：1987-11-17

  A process for the synthesis, in liquid phase and by fragments, of hGRF 1-44 and hGRF 1-40. This process consists in coupling, one after the other and in the order of the sequence of the GRF, (1) on the one hand, the following fragments: ______________________________________ H--Ala--Arg--Ala--Arg--Leu--NH.sub.2 called hGRF Frag- (40-44) or ment A alaninamide (40) H--Gln--Glu--Arg--Gly--OH called hGRF Frag- (36-39) ment B'.sub.1 H--Glu--Ser--Asn--OH called hGRF Frag- (33-35) ment B'.sub.2 H--Ser--Arg--Gln--Gln--Gly--OH called hGRF Frag- (28-32) ment C H--Leu--Gln--Asp--Ile--Met--OH called hGRF Frag- (23-27) ment D' H--Arg--Lys--Leu--OH called hGRF Frag- (20-22) ment E'.sub.1 ______________________________________ PA0 to obtain the peptide K.sub.1 [(hGRF (20-44)] on the corresponding peptide having the sequence (20-40) and PA0 (2) on the other hand, the following fragments: ______________________________________ H--Gln--Leu--Ser--Ala called hGRF Frag- (16-19) ment F.sub.1 H--Tyr--Arg--Lys--Val--Leu--Gly OH called hGRF Frag- (10-15) ment G.sub.1 H--Ile--Phe--Thr--Asn--Ser--OH called hGRF Frag- (5-9) ment H.sub.1 ______________________________________ PA0 to obtain the peptide J [hGRF (5-19)] and thereafter to couple together the peptides J and K.sub.1 in order to form the peptide having the sequence hGRF (5-44) or hGRF (5-40) and finally to couple the resulting peptide with the peptide H-Tyr-Ala-Asp-Ala-H, called fragment I hGRF (1-4).

  一种在液相中通过片段合成hGRF 1-44和hGRF 1-40的方法。该方法包括按照GRF序列的顺序依次耦合以下片段：(1)一方面，以下片段：______________________________________H--Ala--Arg--Ala--Arg--Leu--NH.sub.2，称为hGRF Frag-(40-44)或片段A alaninamide (40)H--Gln--Glu--Arg--Gly--OH，称为hGRF Frag-(36-39)片段B'.sub.1H--Glu--Ser--Asn--OH，称为hGRF Frag-(33-35)片段B'.sub.2H--Ser--Arg--Gln--Gln--Gly--OH，称为hGRF Frag-(28-32)片段CH--Leu--Gln--Asp--Ile--Met--OH，称为hGRF Frag-(23-27)片段D'H--Arg--Lys--Leu--OH，称为hGRF Frag-(20-22)片段E'.sub.1______________________________________ PA0以得到具有序列(20-40)的相应肽K.sub.1 [（hGRF（20-44））]和PA0（2）另一方面，以下片段：______________________________________H--Gln--Leu--Ser--Ala，称为hGRF Frag-(16-19)片段F.sub.1H--Tyr--Arg--Lys--Val--Leu--Gly OH，称为hGRF Frag-(10-15)片段G.sub.1H--Ile--Phe--Thr--Asn--Ser--OH，称为hGRF Frag-(5-9)片段H.sub.1______________________________________ PA0以得到肽J [hGRF（5-19）]，然后将肽J和K.sub.1耦合在一起，以形成具有序列hGRF（5-44）或hGRF（5-40）的肽，最后将所得的肽与称为片段I hGRF（1-4）的肽H-Tyr-Ala-Asp-Ala-H耦合在一起。
• Synthesis of hGRF (Somatocrinin) in liquid phase and intermediate
  申请人：Sanofi

  公开号：US04797469A1

  公开（公告）日：1989-01-10

  A process for the synthesis, in liquid phase and by fragments, of hGRF 1-44 and hGRF 1-40. This process consists in coupling, one after the other and in the order of the sequence of the GRF, (1) on the one hand, the following fragments: __________________________________________________________________________ H--Ala--Arg--Ala--Arg--Leu--NH.sub.2 called Fragment A hGRF (40-44) or alaninamide (40) H--Gln--Glu--Arg--Gly--OH called Fragment B'.sub.1 hGRF (36-39) H--Glu--Ser--Asn--OH called Fragment B'.sub.2 hGRF (33-35) H--Ser--Arg--Gln--Gln--Gly--OH called Fragment C hGRF (28-32) H--Leu--Gln--Asp--Ile--Met--OH called Fragment D' hGRF (23-27) H--Arg--Lys--Leu--OH called Fragment E'.sub.1 hGRF (20-22) __________________________________________________________________________ PAL to obtain the peptide K.sub.1 [(hGRF (20-44)] on the corresponding peptide having the sequence (20-40) and PA1 (2) on the other hand, the following fragments: __________________________________________________________________________ H--Gln--Leu--Ser--Ala called Fragment F.sub.1 hGRF (16-19) H--Tyr--Arg--Lys--Val--Leu--Gly OH called Fragment G.sub.1 hGRF (10-15) H--Ile--Phe--Thr--Asn--Ser--OH called Fragment H.sub.1 hGRF (5-9) __________________________________________________________________________ PAL to obtain the peptide J [hGRF (5-19)] and thereafter to couple together the peptides J and K.sub.1 in order to form the peptide having the sequence hGRF (5-44) or hGRF (5-40) and finally to couple the resulting peptide with the peptide H-Tyr-Ala-Asp-Ala-OH, called fragment I hGRF (1-4).

  一种在液相中通过片段合成hGRF 1-44和hGRF 1-40的过程。该过程包括按照GRF序列的顺序依次耦合以下片段：__________________________________________________________________________ H-阿拉-精-阿拉-精-亮-NH.sub.2，称为片段A hGRF（40-44）或alaninamide（40） H-谷-谷-精-甘-OH，称为片段B'.sub.1 hGRF（36-39） H-谷-丝-天冬氨酸-OH，称为片段B'.sub.2 hGRF（33-35） H-丝-精-谷-谷-甘-OH，称为片段C hGRF（28-32） H-亮-谷-天冬氨酸-异亮-甲硫氨酸-OH，称为片段D' hGRF（23-27） H-精-赖-亮-OH，称为片段E'.sub.1 hGRF（20-22） __________________________________________________________________________ 从相应的具有序列（20-40）的肽K.sub.1 [（hGRF（20-44））]和PA1中获得肽J [hGRF（5-19）]的片段。然后将肽J和K.sub.1耦合在一起，以形成具有序列hGRF（5-44）或hGRF（5-40）的肽，最后将所得肽与片段H-Tyr-Ala-Asp-Ala-OH耦合，称为片段I hGRF（1-4）。
• Synthesis of hpGRF (Somatocrinin) in liquid phase and intermediate
  申请人：Sanofi

  公开号：US04581168A1

  公开（公告）日：1986-04-08

  The invention relates to synthesis of hpGRF (Somatocrinin) in liquid phase and to intermediate peptides, comprising:--coupling, one after the other and in the order of the sequence of the GRF, the fragments in which: (a) the side acid functions of the aspartic and glutamic acids and the side amine function of the lysine are protected by protector groups stable in the conditions of deprotection of the group Boc, (b) the guanidine function of the arginine is protected by protonation, and (c) the N-terminal amino acid is protected on the amine by the Boc group;--selectively eliminating the group Boc from the N-terminal amine of the peptide in phase of elongation by hydrolysis with trifluoroacetic acid, said coupling being effected in an aprotic polar solvent and--eliminating, at the end of sequence, all the protector groups by hydrolysis with the aid of a 0.1 to 1M solution of methanesulfonic or trifluoromethanesulfonic acid in trifluoroacetic acid.

  本发明涉及在液相中合成hpGRF（生长激素释放肽）及其中间肽段的方法，包括以下步骤： 1. 按照GRF序列的顺序，依次连接肽段，其中： （a）使用在去保护Boc基团的条件下稳定的保护基团保护天冬氨酸和谷氨酸的侧链酸基团和赖氨酸的侧链胺基团； （b）使用质子化保护精氨酸的鸟氨酸基团； （c）使用Boc基团保护N-末端氨基酸的胺基团。 2. 在无极性极性溶剂中进行耦合，并在延伸阶段通过三氟乙酸水解有选择地去除肽的N-末端胺基酸上的Boc基团。 3. 在序列末端，通过在三氟乙酸中使用0.1至1M的甲烷磺酸或三氟甲磺酸溶液水解去除所有保护基团。