N-tert-butoxycarbonyl O-allyl L-seryl α,α-dimethylglycyl L-valine methyl ester | 1158995-06-2

• 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: N-tert-butoxycarbonyl O-allyl L-seryl α,α-dimethylglycyl L-valine methyl ester
• 英文别名: (6S,12S)-methyl 6-(allyloxymethyl)-12-isopropyl-2,2,9,9-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate；Boc-Ser(All)-Aib-Val-OMe；N-(tert-butoxycarbonyl)-O-allyl-L-seryl-α-aminoisobutyryl-L-valine methyl ester；N-(tert-Butoxycarbonyl)-O-allyl-L-seryl-alpha-aminoisobutyryl-L-valine methyl ester；methyl (2S)-3-methyl-2-[[2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-prop-2-enoxypropanoyl]amino]propanoyl]amino]butanoate
• CAS: 1158995-06-2
• 化学式: C₂₁H₃₇N₃O₇
• 分子量: 443.541
• InChiKey: VSQHTOQWESSNAL-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl O-allyl L-seryl α,α-dimethylglycyl L-valine methyl ester 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N-tert-butoxycarbonyl O-allyl L-seryl α,α-dimethylglycyl L-valine
  参考文献：
  名称：

  Compounds, compositions and use

  摘要：

  一种肽，包括式（I）的单元，分子量小于2000，其中每个X独立地是一个有机基团，例如C1-6烷基或C1-6烯基基团，首选为—CH2—CH═CH2，或者两个X基团一起形成两个O基团之间的共价或非共价连接，首选为C1-10饱和或不饱和碳链，可以由O、S、N、P或Si中选择的一个或多个杂原子中断，特别是C3-10碳链，或一个X代表一个叠氮基团，另一个代表一个C2-6-炔基基团；两个Z相同，都是O或S；每个Y独立地是C、CH、CH2、N或NH；R1是H或C1-6烷基；R2是H或C1-6烷基；R5是C1-6烷基基团，首选异丙基；或其盐、酯或前药。

  公开号：

  US08710008B2
• 作为产物：
  描述：

  BOC-L-丝氨酸 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 N-tert-butoxycarbonyl O-allyl L-seryl α,α-dimethylglycyl L-valine methyl ester
  参考文献：
  名称：

  Compounds, compositions and use

  摘要：

  一种肽，包括式（I）的单元，分子量小于2000，其中每个X独立地是一个有机基团，例如C1-6烷基或C1-6烯基基团，首选为—CH2—CH═CH2，或者两个X基团一起形成两个O基团之间的共价或非共价连接，首选为C1-10饱和或不饱和碳链，可以由O、S、N、P或Si中选择的一个或多个杂原子中断，特别是C3-10碳链，或一个X代表一个叠氮基团，另一个代表一个C2-6-炔基基团；两个Z相同，都是O或S；每个Y独立地是C、CH、CH2、N或NH；R1是H或C1-6烷基；R2是H或C1-6烷基；R5是C1-6烷基基团，首选异丙基；或其盐、酯或前药。

  公开号：

  US08710008B2

文献信息

• Synthesis of cyclic peptide analogues of the 310 helical Pro138-Gly144 segment of human aquaporin-4 by olefin metathesis
  作者：Øyvind Jacobsen、Jo Klaveness、Ole Petter Ottersen、Mahmood Reza Amiry-Moghaddam、Pål Rongved

  DOI：10.1039/b823559g

  日期：——

  Four cyclic pentapeptides and two cyclic heptapeptides modelled on the 310 helical Pro138-Gly144 segment of the water channel aquaporin-4 (AQP4) postulated to mediate adhesive interactions between AQP4 tetramers were synthesised by olefin metathesis. Three related acyclic pentapeptides Boc-Ser(All)-Xaa1-Val-Ser(All)-Gly-OMe (Xaa1 = Val, Aib; Boc = tert-butoxycarbonyl; All = allyl) and Boc-Ser(Bn)-Val-Val-Gly-Gly-OMe

  通过烯烃复分解合成了假定在水通道Aquaporin-4（AQP4）的3 10螺旋Pro138-Gly144片段上模拟的四个环状五肽和两个环状七肽，它们被认为介导了AQP4四聚体之间的粘合相互作用。三个相关的无环五肽Boc-Ser（全部）-Xaa1-Val-Ser（全部）-Gly-OMe（Xaa1 = Val，Aib; Boc =叔丁氧羰基; All =烯丙基）和Boc-Ser（Bn）-Val- Val-Gly-Gly-OMe（Bn =苄基）和两个无环七肽Boc-Pro-Pro-Ser（全部）-Val-Val-Ser（全部）-Gly-OMe和Boc-Pro-Pro-Ser（Bn）还制备了-Val-Val-Gly-Gly-OMe。NMR，CD和IR数据提供了该肽可以进入3 10的证据。在非极性溶剂中具有螺旋结构，并指出了烯烃桥对水性环境中螺旋度的显着稳定作用。因此，我们可以证明使用闭环烯烃复分
• COMPOUNDS, COMPOSITIONS AND USE
  申请人：Jacobsen Oyvind

  公开号：US20120245094A1

  公开（公告）日：2012-09-27

  A peptide comprising a unit of formula (I) and having a molecular weight of less than 2000 wherein each X is independently an organic group, e.g. a C 1-6 alkyl or C 1-6 alkenyl group, preferably —CH 2 —CH═CH 2 , or the two X groups taken together can form a covalent or non-covalent link between the two O groups, preferably a C 1-10 saturated or unsaturated carbon chain optionally interrupted by one or more heteroatoms selected from O, S, N, P, or Si, especially a C 3-10 carbon chain or one X represents an azido group and the other an C2-6-alkynyl group; both Z's are the same and are O or S; each Y is independently C, CH, CH 2 , N or NH; R 1 is H or C 1-6 alkyl; R 2 is H or C 1-6 alkyl; R 5 is a C 1-6 alkyl group, preferably isopropyl; or a salt, ester or prodrug thereof.

  一种肽，包括公式（I）的一个单元，并且分子量小于2000，其中每个X都是独立的有机基团，例如C1-6烷基或C1-6烯基基团，优选为—CH2—CH═CH2，或者两个X基团可以形成两个O基团之间的共价或非共价连接，优选为C1-10饱和或不饱和的碳链，可选地由O、S、N、P或Si中的一个或多个杂原子中断，特别是C3-10碳链或一个X代表一个偶氮基团，另一个代表C2-6-炔基基团；两个Z相同且都是O或S；每个Y独立地是C、CH、CH2、N或NH；R1是H或C1-6烷基；R2是H或C1-6烷基；R5是C1-6烷基，优选为异丙基；或其盐、酯或前药。
• <i>N</i>-(<i>tert</i>-Butoxycarbonyl)-<i>O</i>-allyl-<scp>L</scp>-seryl-α-aminoisobutyryl-<scp>L</scp>-valine methyl ester: a protected tripeptide with an allylated serine residue
  作者：Hadgu Girmay Gebreslasie、Øyvind Jacobsen、Carl Henrik Görbitz

  DOI：10.1107/s0108270111029647

  日期：2011.9.15

  The title compound [systematic name (6S, 12S)-methyl 6-(allyloxymethyl)-12-isopropyl-2,2,9,9-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate], C21H37N3O7, containing the little studied O-allyl-l-serine residue [Ser(All)], crystallizes in the monoclinic space group C2 with one molecule in the asymmetric unit. The compound is an analogue of the Ser140-Val142 segment of the water channel aquaporin-4 (AQP4). It forms a distorted type-II beta-turn with a P-II-3(10L)-P-II backbone conformation (P-II is polyproline II). The overall backbone conformation is markedly different from that of the CO(Pro139)-Val142 stretch of rat AQP4, but is quite similar to the corresponding segment of human AQP4, despite significant differences at the level of the individual residues. The side chain of the Ser(All) residue adopts a gauche conformation relative to the backbone CO-C-alpha and C-alpha-N bonds. The H atoms of the two CH2 groups in the Ser(All) side chain are almost eclipsed. The crystal packing of the title compound is divided into one-molecule-thick layers, each layer having a hydrophilic core and distinct hydrophobic interfaces on either side.
• Compounds, compositions and use
  申请人：Jacobsen Oyvind

  公开号：US08710008B2

  公开（公告）日：2014-04-29

  A peptide comprising a unit of formula (I) and having a molecular weight of less than 2000 wherein each X is independently an organic group, e.g. a C1-6 alkyl or C1-6 alkenyl group, preferably —CH2—CH═CH2, or the two X groups taken together can form a covalent or non-covalent link between the two O groups, preferably a C1-10 saturated or unsaturated carbon chain optionally interrupted by one or more heteroatoms selected from O, S, N, P, or Si, especially a C3-10 carbon chain or one X represents an azido group and the other an C2-6-alkynyl group; both Z's are the same and are O or S; each Y is independently C, CH, CH2, N or NH; R1 is H or C1-6 alkyl; R2 is H or C1-6 alkyl; R5 is a C1-6 alkyl group, preferably isopropyl; or a salt, ester or prodrug thereof.

  一种肽，包括式（I）的单元，分子量小于2000，其中每个X独立地是一个有机基团，例如C1-6烷基或C1-6烯基基团，首选为—CH2—CH═CH2，或者两个X基团一起形成两个O基团之间的共价或非共价连接，首选为C1-10饱和或不饱和碳链，可以由O、S、N、P或Si中选择的一个或多个杂原子中断，特别是C3-10碳链，或一个X代表一个叠氮基团，另一个代表一个C2-6-炔基基团；两个Z相同，都是O或S；每个Y独立地是C、CH、CH2、N或NH；R1是H或C1-6烷基；R2是H或C1-6烷基；R5是C1-6烷基基团，首选异丙基；或其盐、酯或前药。