Boc-Ile-Thr-OMe | 100803-67-6

• 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: Boc-Ile-Thr-OMe
• 英文别名: methyl (2S,3R)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]butanoate
• CAS: 100803-67-6；59587-52-9
• 化学式: C₁₆H₃₀N₂O₆
• 分子量: 346.424
• InChiKey: FUBGFDYKRJBLIK-USZNOCQGSA-N

物化性质

• 沸点：
  524.1±45.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Ile-Thr-OMe 在 盐酸 、 4-二甲氨基吡啶 、 三氯溴甲烷 、 二乙胺基三氟化硫 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 75.0h， 生成 (4S,18S)-4,18-di((S)-sec-butyl)-7-methyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.15,8.112,15]tetracosa-1(21),5(23),7,12(24),14,19(22)-hexaene-2,9,16-trione
  参考文献：
  名称：

  Synthesis of a Microcystis aeruginosa predicted metabolite with antimalarial activity

  摘要：

  The synthesis of a Microcystis aeruginosa predicted metabolite analog of aerucyclamide B was performed. This hexacyclopeptide was obtained from three heterocyclic building blocks by a convergent macrocycle-assembly methodology. The compound exhibited good in vitro antiplasmodial activity (IC50: 0.18 mu M, K1, cholorquine resistant strain). (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.028
• 作为产物：
  描述：

  BOC-L-异亮氨酸 、 L-苏氨酸甲酯盐酸盐 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到Boc-Ile-Thr-OMe
  参考文献：
  名称：

  与氨基酸和肽水相容的光芳基化

  摘要：

  描述了氨基酸和肽的新型光芳基化，其容许水的存在。在N保护的2-叠氮基苯并咪唑类化合物的存在下照射Boc保护的氨基酸会导致羧基末端或侧链的选择性芳基化。新反应也适用于肽。如ESI-MS / MS片段所示，辐照九肽H-SPSYVYHQF-OH还导致酪氨酸侧链选择性芳基化。化学和区域选择性可能将标题反应添加到光亲和标记方法库中。

  DOI：

  10.1002/chem.201402959

文献信息

• Synthetic Study on Peptide Antibiotic Nisin. V. Total Synthesis of Nisin
  作者：Koichi Fukase、Manabu Kitazawa、Akihiko Sano、Kuniaki Shimbo、Shingo Horimoto、Hiroshi Fujita、Akira Kubo、Tateaki Wakamiya、Tetsuo Shiba

  DOI：10.1246/bcsj.65.2227

  日期：1992.8

  Total synthesis of a lanthionine peptide nisin was achieved by the successive condensations of four segments including cyclic lanthionine peptide parts and the C-terminal linear segment including dehydroalanine, followed by the deprotection procedure with anhydrous HF. Modified reaction conditions for the Hofmann degradation were applied to prepare the dehydroalanine residue from the 2,3-diaminopropionic

  羊毛硫氨酸肽乳链菌肽的全合成是通过包括环状羊毛硫氨酸肽部分和 C 端线性部分（包括脱氢丙氨酸）在内的四个部分的连续缩合，然后用无水 HF 进行脱保护程序来实现的。应用改进的霍夫曼降解反应条件从 2,3-二氨基丙酸残基制备脱氢丙氨酸残基。用无水HF进行最终脱保护，脱氢氨基酸残基没有分解，脱氢氨基酸残基通常在酸性介质中不稳定。合成乳链菌肽在所有方面都与天然乳链菌肽完全相同，从而证实了所提出的结构。
• Synthesis of nisin AB dicarba analogs using ring-closing metathesis: influence of sp³versus sp²hybridization of the α-carbon atom of residues dehydrobutyrine-2 and dehydroalanine-5 on the lipid II binding affinity
  作者：Jack C. Slootweg、Eric. F. van Herwerden、Mark. F. M. van Doremalen、Eefjan Breukink、Rob M. J. Liskamp、Dirk T. S. Rijkers

  DOI：10.1039/c5ob00336a

  日期：——

  alanine at position 2 and 5, respectively. The native dehydrobutyrine at position 2 and dehydroalanine at position 5 were introduced as their precursors, namely threonine and serine, respectively, and subsequent dehydration was carried out by EDCI/CuCl as the condensing agent. Both AB-fragment mimics were analyzed in a lipid II binding assay and it was found that the Ala2/Ala5 AB-mimic (2) showed a reduced

  在此描述了两种乳酸链球菌肽AB dicarba类似物的合成，着重于位置2和5的氨基酸修饰。乳酸链球菌肽模拟物是通过线性肽的固相合成，然后通过通过溶液相化学进行闭环复分解和片段组装。两个N末端乳链菌肽AB片段模拟物分别在位置2和5处含有天然的脱氢酪氨酸（Dhb）/脱氢丙氨酸（Dha）氨基酸残基或丙氨酸。分别引入2位的天然脱氢丁胺和5位的脱氢丙氨酸作为其前体，即苏氨酸和丝氨酸，然后通过EDCI / CuCl作为缩合剂进行脱水。在脂质II结合试验中分析了两种AB片段模拟物，发现Ala2 / Ala5 AB模拟物（2）活性降低，而Dhb2 / Dha5 AB模拟物（3）的活性与天然的一样。 AB片段（1）。
• Synthesis of dolastatin I, a cytotoxic cyclic hexapeptide from the sea hare Dolabella auricularia
  作者：Hideo Kigoshi、Shiho Yamada

  DOI：10.1016/s0040-4020(99)00729-2

  日期：1999.10

  Dolastatin I, a cytotoxic cyclic hexapeptide isolated from the Japanese sea hare Dolabella auricularia, was enantioselectively synthesized, which confirmed its stereostructure.

  从日本海兔Dolabella auricularia分离出的细胞毒性环六肽Dolastatin I是对映选择性合成的，证实了其立体结构。
• Rational Design of Bacitracin A Derivatives by Incorporating Natural Product Derived Heterocycles
  作者：Björn Wagner、Dirk Schumann、Uwe Linne、Ulrich Koert、Mohamed A. Marahiel

  DOI：10.1021/ja062906w

  日期：2006.8.1

  Heterocycles display common structural motifs in nonribosomally produced peptides with an enormous impact on their bioactivity. In the case of the branched cyclic Bacitracin A, the thiazoline moiety is manufactured during NRPS peptide chain elongation. Here we describe a method to selectively alter the heterocyclic metal binding subunit of Bacitracin A by the synthesis of heterocyclic building blocks that were successfully coupled to the linear decapeptide and subsequently cyclized using the excised bacitracin PCP-TE bidomain. Utilization of this cyclase allowed the first generation of branched cyclic bacitracin derivatives containing thiazole and oxazoles. The generated bacitracin derivatives showed bactericidal activity, indicating the possibility of altering the biological important heterocyclic subunit and overcoming existing limitations for the application of bacitracin.