Leu-Ser-OMe | 65519-47-3

• 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: Leu-Ser-OMe
• 英文别名: H-Leu-Ser-OMe；methyl (2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-hydroxypropanoate；methyl (2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-hydroxypropanoate
• CAS: 65519-47-3
• 化学式: C₁₀H₂₀N₂O₄
• 分子量: 232.28
• InChiKey: NYVBEJSCXIHLBN-YUMQZZPRSA-N

物化性质

• 沸点：
  427.6±40.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  Leu-Ser-OMe 在 甲醇 作用下， 反应 110.0h， 生成 (2S,5S)-2-hydroxymethyl-5-iso-butyl-3,6-diketopiperazine
  参考文献：
  名称：

  含有杂原子的手性配体。11.光学活性的2-羟甲基哌嗪锌为二乙基锌对苯甲醛的对映选择性加成催化剂

  摘要：

  从对映体纯的丝氨酸开始，以高收率制备了一系列（2 R，5 S）和（2 S，5 S）-2-羟甲基-5-烷基哌嗪1-5，没有任何消旋作用。描述了将这些化合物用作手性催化剂以将二乙基锌对映异构地加成到醛中。本文报道了在不对称合成中使用哌嗪甲醇的第一个实例。

  DOI：

  10.1016/s0957-4166(00)80107-x
• 作为产物：
  描述：

  在 palladium on activated charcoal N-甲基吗啉 、 环己烯 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 Leu-Ser-OMe
  参考文献：
  名称：

  含有杂原子的手性配体。11.光学活性的2-羟甲基哌嗪锌为二乙基锌对苯甲醛的对映选择性加成催化剂

  摘要：

  从对映体纯的丝氨酸开始，以高收率制备了一系列（2 R，5 S）和（2 S，5 S）-2-羟甲基-5-烷基哌嗪1-5，没有任何消旋作用。描述了将这些化合物用作手性催化剂以将二乙基锌对映异构地加成到醛中。本文报道了在不对称合成中使用哌嗪甲醇的第一个实例。

  DOI：

  10.1016/s0957-4166(00)80107-x

文献信息

• Studies of selective Boc removal in the presence of silyl ethers
  作者：Florine Cavelier、Christine Enjalbal

  DOI：10.1016/0040-4039(96)01070-2

  日期：1996.7

  The selective removal of N-Boc protection can be obtained in the presence of either TBDMS or TBDPS ethers. On the basis of promising results from the literature, we first tried sonication, that failed, whereas the exclusive cleavage of the Boc group was successfully achieved by a saturated solution of HCl in ethyl acetate.

  N-Boc保护的选择性去除可以在TBDMS或TBDPS醚存在下获得。基于文献中令人鼓舞的结果，我们首先尝试了超声处理，但失败了，而Boc基团的唯一裂解是通过HCl在乙酸乙酯中的饱和溶液成功实现的。
• Studies on peptides. CXII. Alternative synthesis of heptacosapeptide, a new gastrointestinal polypeptide.
  作者：NOBUTAKA FUJII、WI LEE、HARUAKI YAJIMA、MOTOYUKI MORIGA、KAZUHIKO MIZUTA

  DOI：10.1248/cpb.31.3503

  日期：——

  A recently found gastrointestinal hormone, PHI (heptacosapeptide), was synthesized in a different manner from that of Moroder et al. [Z. Naturforsch., 37b, 772 (1982) ]. Our synthesis was carried out by successive azide condensation of six peptide fragments (23-27, 19-22, 15-18, 11-14, 7-10, and 1-6), followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The deprotected peptide was purified by gel-filtration on Sephadex G-25, followed by ion-exchange chromatography on CM-Biogel A and reverse phase high-performance liquid chromatography on μBondapak C18. The homogeneous product thus obtained produced a remarkable decrease in systemic blood pressure in anesthetized rats. In addition, Nα-biotinyl-PHI was synthesized for histochemical receptor-binding studies.

  最近发现的一种胃肠激素PHI（七十七肽）与Moroder等人合成的方式不同[Z. Naturforsch., 37b, 772 (1982)]。我们的合成是通过六个肽片段（23-27、19-22、15-18、11-14、7-10和1-6）的连续叠加聚合反应进行的，随后用1 M三氟甲烷磺酸-硫醚在三氟乙酸中去保护。去保护的肽通过Sephadex G-25进行凝胶过滤纯化，随后进行CM-Biogel A上的离子交换色谱以及μBondapak C18上的反相高效液相色谱。由此获得的均匀产品在麻醉大鼠中显著降低了全身血压。此外，合成了Nα-生物素化-PHI用于组织化学受体结合研究。
• Norbornene-Constrained Cyclic Peptides with Hairpin Architecture:  Design, Synthesis, Conformation, and Membrane Ion Transport
  作者：Darshan Ranganathan、V. Haridas、Sunita Kurur、R. Nagaraj、E. Bikshapathy、A. C. Kunwar、A. V. S. Sarma、M. Vairamani

  DOI：10.1021/jo9912045

  日期：2000.1.1

  A novel family of hairpin cyclic peptides has been designed on the basis of the use of norbornene units as the bridging ligands. The design is flexible with respect to the choice of an amino acid, the ring size, and the nature of the second bridging ligand as illustrated here with the preparation of a large number of norborneno cyclic peptides containing a variety of amino acids in ring sizes varying

  在使用降冰片烯单元作为桥连配体的基础上，已经设计了新的发夹环肽家族。如此处所示，在氨基酸选择，环大小和第二个桥连配体的性质方面，设计很灵活，其中制备了大量的降冰片烯环肽，这些环肽含有各种氨基酸，环大小各不相同从12到29元，第二个桥连配体的选择是刚性降冰片烯（11、13a，b），金刚烷单元（7a，b和8）或柔性胱氨酸残基（4a，b和10） ）。内置手柄（作为受保护的COOH基团）的存在允许连接此处所示的Leu-Leu，Val-Val或Aib-Aib侧基分别连接在4b，7b和13b中的各种亚基。如（1）1 H NMR和CD光谱所示，这类新型的受限环肽被证明采用β-折叠或发夹状构象。膜离子迁移研究表明，对称放置在环外部的含有Leu-Leu或Val-Val侧基的降冰片烯环肽4b和7b在运输特定单价阳离子方面显示出高效率和选择性。该性质可归因于降冰片烯单元诱导的发夹状结构，因为在外部包含两对Leu
• Demonstration of <i>e</i><i>ndo</i>-<i>cis</i>-(2<i>S</i>,3<i>R</i>)-Bicyclo[2.2.1]hept-5-en-2,3- dicarbonyl Unit as a Reverse-Turn Scaffold and Nucleator of Two-Stranded Parallel β-Sheets:  Design, Synthesis, Crystal Structure, and Self-Assembling Properties of Norborneno Peptide Analogues
  作者：Darshan Ranganathan、V. Haridas、Sunita Kurur、Achamma Thomas、K. P. Madhusudanan、R. Nagaraj、A. C. Kunwar、A. V. S. Sarma、Isabella L. Karle

  DOI：10.1021/ja980143+

  日期：1998.8.1

  endo-cis-(2S,3R)-Bicyclo[2.2.1]hept-5-en (norbornene) dicarbonyl unit with a built-in U-architecture has been demonstrated to be an excellent reverse-turn molecular scaffold. A large variety of endo-cis-(2S,3R)-norborneno bispeptides containing almost all of the coded amino acids were synthesized and examined for conformational preferences by H-1 NMR, FT-IR, CD, and X-ray crystallographic studies. While FT-IR and H-1 NMR variable-temperature studies ruled out the presence of any significant amount of intramolecular hydrogen bonding in simple bispeptides (3a-h) (except in Aib bispeptide), the CD studies were clearly in favor of a beta-turn type structure. Single-crystal X-ray studies on Aib, Val and Leu containing norborneno bispeptides (3b-d) provided convincing proof for the presence of reverse-turn conformation. While the interstrand C-alpha-C-alpha' distances (5.2-5.7 Angstrom) were well within the range of those for beta-turn structures, no interstrand intramolecular hydrogen bonding was seen in Val and Leu bispeptides; the Aib bispeptide forms a seven-membered hydrogen-bonded ring, thus, showing that the norbornene (2S,3R)-dicarbonyl template assembles peptide chains in reverse-turn conformation by virtue of its built-in U-shaped architecture at these positions, and hydrogen bonding may not be necessary to stabilize the turn structure. The endo-cis-(2S,3R) orientation of bispeptide chains is essential for turn structure as shown by the crystal structure of trans-(2R, 3R) and trans-(2S,3S) derivative of Val bispeptide wherein the two peptide chains move away from each other with the C-alpha-C-alpha' distance increasing to 7.1-8.2 Angstrom. The norbornene 5,6-double bond was hydrogenated to 5,6-dihydro derivative which showed almost the same CD spectrum as its olefinic analogue. Oxidative cleavage [Ru (VIII)] of the 5,6-double bond in norborneno bispeptides, as demonstrated with Leu bispeptide, afforded novel cyclopentanoid peptide analogues. The promise of norbornene unit as a template for nucleating the formation of two-stranded parallel beta-sheets with minimum structural complexity is shown by the preparation of higher members of norborneno bispeptides with the general structure NBE(Pep)(2) [NBE = endo-cis-(2S,3R)-bicyclo[2.2.1]hept-5-en (norbornene) dicarbonyl unit; Pep = peptide strand with two, three, or four (same or different) amino acid residues]. In H-1 NMR, the high (3)J(HN alpha) values (7.0-9.3 Hz) observed for the amide protons (Table 5) coupled with the presence of medium to strong intrastrand sequential ROE connectivities d(alpha N(i,i+1)) spanning the entire three- or four-residue sequence in the peptide strands of 9a-e and 10 and the exhibition of relatively low-temperature coefficients (d delta/dT = -0.2 to -3.4 ppb/K) for amide protons in DMSO-d(6) solvent (Table 4) clearly suggested that hydrogen-bonded beta-sheet conformers dominate the population. FT-IR and CD studies provided further support for parallel beta-sheet structures. A particularly unique feature of the norborneno bispeptides is their strong tendency to self-assemble in the solid state.Thus, while endo-cis-(2S,3R)-Aib bispeptide (3b) forms 16-membered hydrogen bonded centrosymmetric dimers, the half-ester half-acid and the dicarboxylic acid derivatives of 3b self-assemble to form highly ordered hydrogen-bonded molecular ribbons. The Val and Leu cis-(2S, 3R)-bispeptides organize into hydrogen-bonded chains and the trans isomer of Val bispeptide self-assembles into hydrogen-bonded beta-sheet ribbon.
• Chiral ligands containing heteroatoms. 11. Optically active 2-hydroxymethyl piperazincs as catalysts in the enantioselective addition of diethylzinc to benzaldehyde
  作者：Massimo Falorni、Michele Satta、Sandra Conti、Giampaolo Giacomelli

  DOI：10.1016/s0957-4166(00)80107-x

  日期：1993.11

  (2R,5S) and (2S,5S)-2-hydroxymethyl-5-alkyl piperazines 1–5 were prepared in good yields without any racemization. The use of these compounds as chiral catalysts for the enantioselective addition of diethylzinc to aldehydes is described. This paper reports the first example of the use of piperazine methanols in asymmetric synthesis.

  从对映体纯的丝氨酸开始，以高收率制备了一系列（2 R，5 S）和（2 S，5 S）-2-羟甲基-5-烷基哌嗪1-5，没有任何消旋作用。描述了将这些化合物用作手性催化剂以将二乙基锌对映异构地加成到醛中。本文报道了在不对称合成中使用哌嗪甲醇的第一个实例。