Z(OMe)-Ala-OSu | 109304-95-2

• 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: Z(OMe)-Ala-OSu
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]propanoate
• CAS: 109304-95-2
• 化学式: C₁₆H₁₈N₂O₇
• 分子量: 350.328
• InChiKey: HMJKFBWJWCFNHG-JTQLQIEISA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111.24
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Z(OMe)-Ala-OSu 在 三乙胺 、 三氟乙酸 、 锌 作用下， 以 溶剂黄146 为溶剂， 生成 Z(OMe)-Ala-Asp(OMen)-Leu-NHNH2
  参考文献：
  名称：

  肽的研究。CLIV。合成36个残基的酰胺肽，其对应于人胰多肽的整个氨基酸序列。

  摘要：

  通过溶液法合成了与人类胰腺多肽（hPP）的整个氨基酸序列相对应的36个残基肽。使用了一种新的天冬氨酸衍生物，即天冬氨酸（OMen）[Men = 薄荷基]。七个片段用于构建hPP的肽骨架，所有保护基团均通过2 M三甲基硅烷三氟甲烷磺酸酯二苯基硫醚/三氟乙酸裂解。合成的肽抑制了大鼠胰腺的蛋白质分泌。

  DOI：

  10.1248/cpb.35.3585

文献信息

• Synthesis of an immunologically active fragment analog of prothymosin .ALPHA. with enhanced enzymatic stability.
  作者：Takashi ABIKO、Hiroshi SEKINO

  DOI：10.1248/cpb.39.752

  日期：——

  A fragment analog, [D-Arg30]prothymosin α fragment 1-30, containing D-arginine in place of arginine residue at position 30 was synthesized by the liquid phase procedure and studied for immunological effect on the impaired blastogenic response of T-lymphocytes isolated from uremic patients after treatment of human serum. Deacetyl-thymosin α1, a synthetic octaeicosapeptide corresponding to deacetyl-prothymosin α fragment 1-28, has restoration ability for the impaired blastogenic response of T-lymphocytes of uremic patients but is susceptible to proteolytic digestion. On the other hand, the fragment analog, [D-Arg30]prothymosin α fragment 1-30 retained activity and was shown to exhibit a high degree of stability when incubated in human serum. These results indicate that N-terminal acetylation and the introduction of D-residue into the C-terminal residue of prothymosin α fragment 1-30 increase resistance to proteolytic degradation by exopeptidases.

  通过液相法合成了一种片段类似物[D-Arg30]胸腺肽α片段1-30，该片段含有D-精氨酸，取代了第30位的精氨酸残基。脱乙酰胸腺肽α1是一种与脱乙酰胸腺肽α片段1-28相对应的合成八代肽，它对尿毒症患者T淋巴细胞受损的鼓泡生成反应具有恢复能力，但易被蛋白酶消化。另一方面，片段类似物[D-Arg30]原胸腺肽α片段 1-30 保留了活性，并且在人血清中培养时表现出高度稳定性。这些结果表明，原胸腺肽α片段1-30的N端乙酰化和在C端残基中引入D-残基可增强对外肽酶蛋白分解的抵抗力。
• Synthesis of a 37-residue peptide amide corresponding to the entire amino acid sequence of .ALPHA.-form of rat calcitonin gene-related peptide (.ALPHA.-rCGRP).
  作者：KENSHI ANDO、KOUKI KITAGAWA、SHINYA KIYAMA、TATSUHIKO KAWAMOTO、TADASHI AKITA、ITSUO YAMAMOTO、KANJI TORIZUKA

  DOI：10.1248/cpb.35.60

  日期：——

  The heptatriacontapeptide amide corresponding to the entire amino acid sequence of α-form of rat calcitonin gene-related peptide (α-rCGRP) was synthesized by the conventional solution method. All protecting groups employed were removed by treatment with 1 M trifluoromethanesulfonic acid-thioanisole-trifluoroacetic acid, and the deprotected peptide was subjected to airoxidation to form the intramolecular disulfide bond. After purification by gel-filtration on Sephadex G-50, followed by reversed-phase high performance liquid chromatography, a highly purified sample of synthetic α-rCGRP was obtained. In terms of suppression of bone 45Ca-release stimulated by synthetic human parathyroid hormone (1-34), synthetic α-rCGRP was as active as synthetic human CGRP.

  采用传统的溶液法合成了与大鼠降钙素基因相关肽（α-rCGRP）的整个氨基酸序列相对应的七胜肽酰胺。用 1 M 三氟甲磺酸-硫代苯甲醚-三氟乙酸去除所有保护基团，然后对去保护基团的肽进行氧化反应以形成分子内二硫键。经 Sephadex G-50 凝胶过滤纯化后，再经反相高效液相色谱纯化，就得到了高度纯化的合成 α-rCGRP 样品。在抑制合成人甲状旁腺激素（1-34）刺激的骨 45Ca 释放方面，合成 α-rCGRP 与合成人 CGRP 具有同样的活性。
• Studies on peptides. CLXIV. Solution-phase synthesis of a 36-residue peptide amide corresponding to the entire amino acid sequence of chicken antral peptide.
  作者：LILI Guo、EIGORO MURAYAMA、SUSUMU FUNAKOSHI、NOBUTAKA FUJII、MITSURU AONO、MASAYUKI MATSUDA、MOTOYUKI MORIGA、HARUAKI YAJIMA

  DOI：10.1248/cpb.36.4364

  日期：——

  A 36-residue peptide amide corresponding to the entire amino acid sequence of chicken antral peptide was synthesized by assembling seven peptide fragments via the azide, followed by thioanisole-mediated deprotection with trimethylsilyl bromide and trimethylsilyl trifluoromethanesulfonate in trifluoroacetic acid.The synthetic peptide stimulated gastric secretion, but not pancreatic secretion.

  通过叠氮化物组装七个肽片段，然后在三氟乙酸中用三甲基溴硅烷和三氟甲磺酸三甲基硅烷酯介导的硫代茴香醚介导的去保护，合成了对应于鸡胃窦肽的整个氨基酸序列的36个残基的肽酰胺。合成的肽刺激胃液分泌，但不是胰腺分泌。
• Solution synthesis of human neuropeptide Y (hNPY).
  作者：Seishi ONO、Kouki KITAGAWA、Shiroh FUTAKI、Shinya KIYAMA、Yoshihiro OOI、Tadashi AKITA、Shunichi HIGASHIDE、Kazutomo INOUE、Syoichiro SUMI、Takayoshi TOBE

  DOI：10.1248/cpb.37.1925

  日期：——

  Human neuropeptide Y (hNPY) was synthesized in a conventional manner by assembling seven peptide fragments followed by reduction of the Met(O) residue with phenylthiotrimethylsilane and subsequent deprotection with 1 M trimethylsilyl trifluoromethanesulfonate (TMSOTf)-thioanisole in trifluoroacetic acid (TFA). Alternatively, deprotection was performed in a two-step manner; first, treatment with 1 M trimethylsilyl bromide-thioanisole in TFA, and then with 1 M TMSOTf-thioanisole in TFA. After purification by gel-filtration on Sephadex G-25, followed by reversed-phase high-performance liquid chromatography, a highly purified sample of synthetic hNPY was obtained in both cases.When administered in dogs, synthetic hNPY was as active as porcine NPY in terms of the effects on systemic arterial blood pressure, pancreatic blood flow, and superior mesentric artery (SMA) blood flow. Met(O)17-hNPY was found to be as active as the parent sample in these bioassays.

  人神经肽 Y（hNPY）的合成采用传统方法，先将七个肽片段组合在一起，然后用苯基硫代三甲基硅烷还原 Met（O）残基，再用 1 M 三甲基硅基三氟甲磺酸盐（TMSOTf）-硫代苯甲醚在三氟乙酸（TFA）中进行脱保护。另一种方法是分两步进行脱保护：首先用 1 M 三甲基硅溴-硫代苯甲醚在 TFA 中进行处理，然后用 1 M 三甲基硅氧烷-硫代苯甲醚在 TFA 中进行处理。在狗体内给药时，合成 hNPY 对全身动脉血压、胰腺血流和心室上动脉（SMA）血流的影响与猪 NPY 一样有效。在这些生物测定中，Met(O)17-hNPY的活性与母体样本相同。
• Studies on peptides. CLVI. Synthesis of second human calcitonin gene-related peptide(.BETA.-hCGRP) by application of a new disulfide-bonding reaction with thallium(III) trifluoroacetate.
  作者：NOBUTAKA FUJII、TOSHIHIRO WATANABE、AKIRA OTAKA、KIYOSHI BESSHO、ITSUO YAMAMOTO、TOSHIHARU NODA、HARUAKI YAJIMA

  DOI：10.1248/cpb.35.4769

  日期：——

  A 37-residue peptide corresponding to the entire amino acid sequence of second human calcitonin gene-related peptide (β-hCGRP) was synthesized by assembling seven peptide fragments, followed by two successive treatments; i.e., first with thallium (III) trifluoroacetate to establish the disulfide bond between two Cys (Ad) residues and then with 1 M trimethylsilyl trifluoromethane-sulfonate/trifluoroacetic acid in the presence of diphenyl sulfide and ammonium iodide to remove all protecting groups employed and at the same time to reduce Met (O) to Met. The result was compared with that obtained by the usual air-oxidation procedure. Synthetic β-hCGRP exhibited a weak inhibitory action against bone Ca-resorption stimulated by [1-34] -parathyroid hormone in vitro and lowered the Ca and Pi levels in rat serum.

  通过将七个肽片段组合在一起，合成了与第二个人类降钙素基因相关肽（β-hCGRP）的整个氨基酸序列相对应的 37 个残基的肽，然后进行了两次连续处理，即先使用三氟乙酸铊（III）在两个 Cys（Ad）残基之间建立二硫键，然后使用 1 M 三甲基硅基三氟甲烷-磺酸盐/三氟乙酸铊（III）处理、先用三氟乙酸铊（III）在两个 Cys（Ad）残基之间建立二硫键，然后在二苯基硫醚和碘化铵存在下用 1 M 三甲基硅基三氟甲烷磺酸盐/三氟乙酸去除所有使用的保护基团，同时将 Met（O）还原为 Met。将结果与通常的空气氧化法进行比较。合成的 β-hCGRP 对体外[1-34] -甲状旁腺激素刺激的骨钙吸收有微弱的抑制作用，并能降低大鼠血清中 Ca 和 Pi 的水平。