5-(二氨基亚甲基氨基)-2-[三(苯基)甲基氨基]戊酸 | 38453-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 5-(二氨基亚甲基氨基)-2-[三(苯基)甲基氨基]戊酸
• 英文名称: N^α-trityl-L-arginine
• 英文别名: N^α-Trityl-L-arginin；N2-trityl-L-arginine；N^α-Trt-L-Arginin；(2S)-5-(diaminomethylideneamino)-2-(tritylamino)pentanoic acid
• CAS: 38453-62-2
• 化学式: C₂₅H₂₈N₄O₂
• 分子量: 416.523
• InChiKey: XOPFDFWTKCSBGX-QFIPXVFZSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  603.3±65.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  5-(二氨基亚甲基氨基)-2-[三(苯基)甲基氨基]戊酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 亚磷酸二乙酯 作用下， 生成 N^α-(N^α-trityl-L-arginyl)-L-tryptophan-methyl ester
  参考文献：
  名称：

  Synth�se de laL-histidyl-L-ph�nylalanyl-L-arginyl-L-tryptophanyl-glycyl-?-CBO-L-lysyl-L-prolyl-L-valylamide

  摘要：

  AbstractTrityl‐glycyl‐ϵ‐CBO‐L‐lysine is condensed with L‐prolyl‐L‐valine methyl ester and, after amidification and splitting of the trityl group, glycyl‐ϵ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valylamide is obtained. This is condensed with ditrityl‐L‐histidyl‐L‐phenylalanyl‐L‐arginyl‐L‐tryptophane prepared by condensation of ditrityl‐L‐histidyl‐L‐phenylalanine with L‐arginyl‐L‐tryptophane methyl ester and saponification. Dicyclohexyl‐carbodiimide is used as a condensing agent. After splitting off the trityl groups, the final octapeptide, L‐histidyl‐L‐phenylalanyl‐L‐arginyl‐L‐tryptophanyl‐glycyl‐ϵ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valylamide is shown to be optically pure by leucine‐aminopeptidase digestion.

  DOI：

  10.1002/hlca.19580410641
• 作为产物：
  描述：

  N^α-trityl-L-arginine methyl ester 生成 5-(二氨基亚甲基氨基)-2-[三(苯基)甲基氨基]戊酸
  参考文献：
  名称：

  Synth�se de laL-histidyl-L-ph�nylalanyl-L-arginyl-L-tryptophanyl-glycyl-?-CBO-L-lysyl-L-prolyl-L-valylamide

  摘要：

  AbstractTrityl‐glycyl‐ϵ‐CBO‐L‐lysine is condensed with L‐prolyl‐L‐valine methyl ester and, after amidification and splitting of the trityl group, glycyl‐ϵ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valylamide is obtained. This is condensed with ditrityl‐L‐histidyl‐L‐phenylalanyl‐L‐arginyl‐L‐tryptophane prepared by condensation of ditrityl‐L‐histidyl‐L‐phenylalanine with L‐arginyl‐L‐tryptophane methyl ester and saponification. Dicyclohexyl‐carbodiimide is used as a condensing agent. After splitting off the trityl groups, the final octapeptide, L‐histidyl‐L‐phenylalanyl‐L‐arginyl‐L‐tryptophanyl‐glycyl‐ϵ‐CBO‐L‐lysyl‐L‐prolyl‐L‐valylamide is shown to be optically pure by leucine‐aminopeptidase digestion.

  DOI：

  10.1002/hlca.19580410641

文献信息

• New process for the synthesis of N alpha-fluorenylmethoxycarbonyl-Ng-trityl-arginine
  申请人：SCLAVO S.p.A.

  公开号：EP0375047A2

  公开（公告）日：1990-06-27

  An improvement is described in the synthesis method for Nα-trityl-­NG-trityl-arginine within a process for preparing Nα-fluorenyl­methoxycarbonyl-NG-trityl-arginine from arginine, comprising: a) forming Nα-trityl-NG-trityl-arginine b) selectively detaching the trityl group from the α-NH₂ and c) introducing the fluorenylmethoxycarbonyl group in its place. The improvement consists of preparing the Nα-trityl-NG-trityl-­arginine by solubilizing the arginine in an aprotic organic solvent by tri-alkylsilylation both of the amino nitrogen and of the carboxyl group, followed by tritylation, with trityl chloride, of the α-amino nitrogen, and of the guanidino group after deprotonating this latter with a bicyclic guanidine. The new improved process can also lead to variable quantities of the arginine analogue di-tritylated at the guanidino group, namely Nα-fluorenylmethoxycarbonyl-NG-di-trityl-arginine. This new compound, to which the present invention also relates, can also be used as such in peptide synthesis.

  在从精氨酸制备 Nα-芴甲氧羰基-NG-三苯甲基-精氨酸的工艺中，对 Nα-三苯甲基-NG-三苯甲基-精氨酸的合成方法进行了改进，包括： 1： a) 形成 Nα-三苯甲基-NG-三苯甲基-精氨酸 b) 选择性地将三苯甲基与 α-NH₂ 分离，以及 c) 在其位置上引入芴甲氧羰基。 改进的方法包括：在非烷基有机溶剂中通过氨基氮和羧基的三烷基硅烷化使精氨酸溶解，然后用三酰氯对α-氨基氮和胍基进行三烷基化，最后用双环胍对胍基进行去质子化，从而制备出 Nα-三苯甲基-NG-三苯甲基-精氨酸。 改进后的新工艺还可以制备出不同数量的在胍基上二三苯甲基化的精氨酸类似物，即 Nα-芴甲氧羰基-NG-二三苯甲基-精氨酸。本发明所涉及的这种新化合物也可用于肽合成。
• New method for alkylating guanidino groups
  申请人：SCLAVO S.p.A.

  公开号：EP0416417A2

  公开（公告）日：1991-03-13

  A method is described for substituting at least one hydrogen atom originally present in the guanidino group of a compound of general formula (I) where R is any substituted or unsubstituted residue, by a group R₁ where R₁ is an unsubstituted or substituted, linear or branched alkyl, consisting of: a) silylating the guanidino group and any other silylatable functional groups present within the R group and b) alkylating the product obtained in step a) with a mixture consisting of the alkyl halide R₁-X and an organic base containing a tertiary nitrogen.

  描述了一种方法，用于取代通式(I)化合物的胍基中原本存在的至少一个氢原子 其中 R 是任何取代或未取代的残基，由基团 R₁取代，其中 R₁ 是未取代或取代的直链或支链烷基，由以下基团组成： a) 将 R 基团中的胍基和任何其他可硅烷化的官能团硅烷化，以及 b) 用由烷基卤化物 R₁-X 和含有叔氮的有机碱组成的混合物对步骤 a) 中得到的产物进行烷基化。
• New arginine derivative, process for the preparation thereof and its use in peptide synthesis
  申请人：ENIRICERCHE S.p.A.

  公开号：EP0277561B1

  公开（公告）日：1992-04-15
• Protection of Some Peptides and Amino Acids by Tritylation
  作者：John Halstrøm、Kay Brunfeldt

  DOI：10.1515/bchm2.1972.353.2.1204

  日期：1972.1
• US5079375A
  申请人：——

  公开号：US5079375A

  公开（公告）日：1992-01-07