L-蛋氨酸烯丙基酯对甲苯磺酸盐 | 142601-87-4

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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
• 中文名称: L-蛋氨酸烯丙基酯对甲苯磺酸盐
• 中文别名: L-蛋氨酸-甲苯-4-磺酸烯丙酯
• 英文名称: L-methionine-allyl ester tosylate
• 英文别名: methionine allyl ester tosylate；Met-O-All*Tos；PTSA*H-Met-OAll；(S)-Allyl 2-amino-4-(methylthio)butanoate 4-methylbenzenesulfonate；4-methylbenzenesulfonic acid;prop-2-enyl (2S)-2-amino-4-methylsulfanylbutanoate
• CAS: 142601-87-4
• 化学式: C₇H₈O₃S*C₈H₁₅NO₂S
• mdl: MFCD00077939
• 分子量: 361.483
• InChiKey: FBJFDYRGTDWIKF-FJXQXJEOSA-N

物化性质

• 熔点：
  114-116 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  2930909090
• 储存条件：
  2-8°C，干燥

反应信息

• 作为反应物：
  描述：

  BOC-L-苯丙氨酸 、 L-蛋氨酸烯丙基酯对甲苯磺酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以43%的产率得到Boc-Phe-Met-OAll
  参考文献：
  名称：

  基于轮烷的前肽：生物活性五肽的保护和酶促释放

  摘要：

  保护环：[2]轮烷1保护并选择性释放生物活性五肽。轮烷大环化合物提供了一种防御性屏障，可极大地改善该肽对单个肽酶和人血浆中存在的酶混合物的不良稳定性。轮烷中糖苷酶催化的碳水化合物“终止子”的裂解触发母体肽的释放（见图）。

  DOI：

  10.1002/anie.200903215
• 作为产物：
  描述：

  L-蛋氨酸 、 对甲苯磺酸 、 烯丙醇 以 甲苯 为溶剂， 以82%的产率得到L-蛋氨酸烯丙基酯对甲苯磺酸盐
  参考文献：
  名称：

  基于轮烷的前肽：生物活性五肽的保护和酶促释放

  摘要：

  保护环：[2]轮烷1保护并选择性释放生物活性五肽。轮烷大环化合物提供了一种防御性屏障，可极大地改善该肽对单个肽酶和人血浆中存在的酶混合物的不良稳定性。轮烷中糖苷酶催化的碳水化合物“终止子”的裂解触发母体肽的释放（见图）。

  DOI：

  10.1002/anie.200903215

文献信息

• Total Enzymatic Synthesis of the Cholecystokinin Octapeptide (CCK‐8)
  作者：Rajendra Joshi、Liping Meng、Heiner Eckstein

  DOI：10.1002/hlca.200890128

  日期：2008.6

  The Bz-Arg group was used as an N-terminal protecting group in the synthesis of the tripeptide fragment. The protected CCK-8 was treated with trypsin to remove the Bz-Arg group successfully. Free or immobilized enzymes were used as catalysts. The effect of the acyl donor ester structure, the C(α) protecting group of the nucleophile, reaction media, enzyme, and the carrier of the enzymes on the outcome

  报道了胆囊收缩素八肽（CCK-8）的酶促合成。靶八肽CCK-8是具有与天然胆囊收缩素相同的生物学活性的最小活性序列，并且是控制胃肠功能的潜在治疗剂，并且是治疗癫痫和肥胖症的候选药物。通过将Bz-Arg-Asp（OEt）-Tyr-Met-OAl和Gly-Trp-Met-Asp（OMe）-Phe-NH 2与固定的α一起孵育获得受保护的CCK-8-胰凝乳蛋白酶。在三肽片段的合成中，Bz-Arg基团被用作N端保护基。用胰蛋白酶处理受保护的CCK-8，以成功去除Bz-Arg基团。游离的或固定的酶用作催化剂。研究了酰基给体酯结构，亲核试剂的C（α）保护基，反应介质，酶和酶载体对偶联反应结果的影响。
• Synthesis and Membrane Binding Properties of a Lipopeptide Fragment from Influenza Virus A Hemagglutinin
  作者：Frank Eisele、Jürgen Kuhlmann、Herbert Waldmann

  DOI：10.1002/1521-3765(20020802)8:15<3362::aid-chem3362>3.0.co;2-0

  日期：2002.8.2

  Hemagglutinin from influenza virus A is a S-palmitoylated lipoglycoprotein in which the lipid groups are thought to influence the interaction between cell membrane and capsid during budding of viral offspring as well as fusion processes of the viral membrane with the endosome after entry of the viral particle into the cell. The paper describes the development of a method for the synthesis of characteristic lipidated hemagglutinin derived peptides which additionally carry the fluorescent 7-nitrobenz-2oxa-1,3-diazole (NBD) group. To achieve this goal the enzyme-sensitive para-phenylacetoxybenzyloxycarbonyl (PAOB) ester was developed. It is cleaved from the peptides and lipidated peptides under very mild conditions and with complete selectivity by treatment with the enzyme penicillin G acylase; this results in the formation of a phenolate. This intermediate spontaneously undergoes fragmentation thereby releasing the desired carboxylates. The combined use of this enzymelabile fragmenting ester with the acidlabile Boc group, the Pd-0-sensitive allyl ester and the corresponding Aloc urethane gave access to a mono-S-palmitoylated and a doubly S-palmitoylated NBD-labelled hemagglutinin peptide. The binding of these lipopeptides to model membranes was analyzed in a biophysical setup monitoring the transfer of fluorescent-labelled lipopeptide from vesicles containing the non-ex-changeable fluorescence quencher Rho-DHPE to quencher-free vesicles. The experiments demonstrate that one lipid group is not sufficient for quasi-irreversible membrane insertion of lipidated peptides. This is, however, achieved by introduction of the bis-palmitoyl anchor. The intervesicle transfer always implies release of peptides localized at the outer face of the vesicles into solution followed by diffusion to and insertion into acceptor vesicles. For peptides bound at the inner face of the vesicle membrane, however, an additional flip-flop diffusion to the outer face has to occur beforehand. The kinetics of these processes were estimated by fast chemical quench of the outside fluorophores by sodium dithionite.
• Rotaxane-Based Propeptides: Protection and Enzymatic Release of a Bioactive Pentapeptide
  作者：Anthony Fernandes、Aurélien Viterisi、Frédéric Coutrot、Stéphanie Potok、David A. Leigh、Vincent Aucagne、Sébastien Papot

  DOI：10.1002/anie.200903215

  日期：2009.8.17

  Ring of protection: A [2]rotaxane 1 protects and selectively releases a bioactive pentapeptide. The rotaxane macrocycle provides a defensive shield that very significantly improves the poor stability of the peptide to both individual peptidases and the cocktail of enzymes present in human plasma. Glycosidase‐catalyzed cleavage of a carbohydrate ‘stopper’ in the rotaxane triggers release of the parent

  保护环：[2]轮烷1保护并选择性释放生物活性五肽。轮烷大环化合物提供了一种防御性屏障，可极大地改善该肽对单个肽酶和人血浆中存在的酶混合物的不良稳定性。轮烷中糖苷酶催化的碳水化合物“终止子”的裂解触发母体肽的释放（见图）。