serine-proline | 23827-93-2

• 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: serine-proline
• 英文别名: H-Ser-Pro-OH；Ser-Pro；SP-OH；SP；1-L-seryl-L-proline；1-L-Seryl-L-prolin；(2S)-1-[(2S)-2-azaniumyl-3-hydroxypropanoyl]pyrrolidine-2-carboxylate
• CAS: 23827-93-2
• 化学式: C₈H₁₄N₂O₄
• mdl: MFCD00037333
• 分子量: 202.21
• InChiKey: WBAXJMCUFIXCNI-WDSKDSINSA-N

物化性质

• 沸点：
  524.0±50.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  serine-proline 在 钯 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 48.0h， 生成 Gly-L-Ala-Ser-Pro
  参考文献：
  名称：

  缓激肽片段及其类似物在苯丙氨酸残基上的合成。

  摘要：

  合成了缓激肽片段及其类似物 Gly-X-Ser-Pro（X：L-Phe I、D-Phe II、L-Ala III、D-Ala IV、β-Ala V 和 Gly VI）和 X-Ser-Pro（X：L-Phe VII 和 D-Phe VIII）。化合物 I、II、V、VII 和 VIII 延长了戊巴比妥诱导的小鼠睡眠时间，每只小鼠的用量为 2.5 nmol。

  DOI：

  10.1248/cpb.28.310
• 作为产物：
  描述：

  在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 serine-proline
  参考文献：
  名称：

  Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,

  摘要：

  Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of L-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-L-Pro, L-Ala-L-Pro, and N-acyl derivatives of L-Pro. The best substrate identified to date is N-acetyl-L-Pro with a value of k(cat)/K-m of 3 x 10(5) M-1 s(-1). Sgx9260b catalyzes the hydrolysis of L-hydrophobic L-Pro dipeptides and N-acyl derivatives of L-Pro. The best substrate identified to date is N-propionyl-L-Pro with a value of k(cat)/K-m of 1 x 10(5) M-1 s(-1). Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (beta/alpha)(8)-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of L-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The a-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows beta-strand 7 within the (beta/alpha)(8)-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of L-arginine (PDB code 3MTW).

  DOI：

  10.1021/bi100897u

文献信息

• Amino acid derivatives as antihypertensives
  申请人：Merck & Co., Inc.

  公开号：US04472380A1

  公开（公告）日：1984-09-18

  There are disclosed processes for preparing carboxyalkyl dipeptide derivatives and related compounds which are useful as angiotension converting enzyme (ACE) inhibitors and as antihypertensives and pharmaceutical compositions containing these carboxyalkyl dipeptide compounds in combination with another antihypertensive and/or diuretic compound.

  本发明公开了制备羧基烷基二肽衍生物及其相关化合物的方法，这些化合物可用作血管紧张素转换酶（ACE）抑制剂和降压剂，并且与另一种降压剂和/或利尿剂化合物结合在一起的药物组合物中含有这些羧基烷基二肽化合物。
• Aminoacid derivatives as antihypertensives
  申请人：Merck & Co., Inc.

  公开号：US04374829A1

  公开（公告）日：1983-02-22

  The invention relates to new carboxyalkyl dipeptide derivatives and related compounds which are useful as antihypertensives.

  本发明涉及新的羧基烷基二肽衍生物及相关化合物，其可用作降压剂。
• ALZHEIMER'S DISEASE THERAPEUTICS BASED ON PIN-1 CATALYZED CONFORMATIONAL CHANGES IN PHOSPHORYLATED AMYLOID PRECURSOR PROTEIN
  申请人：LU Ping Kun

  公开号：US20080058276A1

  公开（公告）日：2008-03-06

  The present invention is directed to inhibiting amyloidogenic processing of amyloid precursor protein, and/or inhibiting production of amyloid beta peptides. These methods can involve accelerating cis/trans isomerization of amyloid precursor protein at a phosphorylated serine/threonine-proline motif and/or contacting a cell with a compound that mimics the cis conformation of a phosphorylated serine/threonine-proline motif of an amyloid precursor protein. The present invention also relates to treating and/or preventing in a subject a degenerative neurological disease characterized by amyloidogenic processing of amyloid precursor protein and/or overproduction of amyloid beta peptide. This method involves administering an agent that accelerates cis/trans isomerization of amyloid precursor protein at a phosphorylated serine/threonine-proline motif and/or inhibits production of amyloid β peptides. Methods of screening for therapeutic agents effective in treating and/or preventing such diseases, methods of screening for biological molecules involved in the amyloidogenic pathway, and compounds that mimic the cis conformation of a phosphorylated serine/threonine-proline motif of an amyloid precursor protein are also disclosed.

  本发明旨在抑制淀粉样前体蛋白的淀粉样加工，并/或抑制淀粉样β肽的产生。这些方法可以涉及加速磷酸化丝氨酸/苏氨酸-脯氨酸基序的淀粉样前体蛋白的顺反异构化，和/或用类似于淀粉样前体蛋白磷酸化丝氨酸/苏氨酸-脯氨酸基序的顺式构象的化合物接触细胞。本发明还涉及用于治疗和/或预防患有淀粉样前体蛋白淀粉样加工和/或淀粉样β肽过度产生的退行性神经疾病的方法。该方法涉及给予一种能加速淀粉样前体蛋白磷酸化丝氨酸/苏氨酸-脯氨酸基序的顺反异构化和/或抑制淀粉样β肽产生的药物。还公开了筛选用于治疗和/或预防此类疾病的治疗剂的方法，筛选参与淀粉样加工途径的生物分子的方法，以及类似于淀粉样前体蛋白磷酸化丝氨酸/苏氨酸-脯氨酸基序的顺式构象的化合物。
• Abderhalden; Bahn, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1932, vol. 210, p. 246,258
  作者：Abderhalden、Bahn

  DOI：——

  日期：——
• Cyclo(<scp>l</scp>-proline-<scp>l</scp>-serine) Dipeptide Suppresses Seed Borne Fungal Pathogens of Rice: Altered Cellular Membrane Integrity of Fungal Hyphae and Seed Quality Benefits
  作者：Baninderjit Kaur Poonia、Anjali Sidhu、Anju Bala Sharma

  DOI：10.1021/acs.jafc.1c07659

  日期：2022.2.23