Boc-Met-Arg-Phe-NH2

• 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-Met-Arg-Phe-NH2
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]carbamate
• 化学式: C₂₅H₄₁N₇O₅S
• 分子量: 551.71
• InChiKey: KTTVOEGNSIQZMX-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  229
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Met-Arg-Phe-NH2 生成 L-Methionyl-N~5~-(diaminomethylidene)-L-ornithyl-L-phenylalaninamide
  参考文献：
  名称：

  OKAI, XIDEHO

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-L-蛋氨酸 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 生成 Boc-Met-Arg-Phe-NH2
  参考文献：
  名称：

  水溶液中的肽合成。一、对二烷基磺基苯酚作为水溶性偶联剂的应用

  摘要：

  发现(对羟基苯基)二甲基锍甲基硫酸盐(HODMSP·MeSO4-)是一种优良的偶联剂，具有水溶性和高反应性；在反应性、产品纯度和外消旋化方面，它与通常的活性酯一样令人满意。HODMSP·MeSO4-活性酯法的显着优势在于，当反应混合物的pH值得到控制时，双功能残基如Arg、Lys、Cys和Tyr可以被选择性地酰化。通过这种新的活性酯方法合成了软体动物神经肽 FMRFamide（Phe-Met-Arg-Phe-NH2），以评估该方法在涉及肽合成的进一步应用中的应用。

  DOI：

  10.1246/bcsj.60.2409

文献信息

• p-Hydroxyphenylsulfonium salts and their use in the preparation of esters and amides
  申请人：SANSHIN KAGAKU KOGYO CO., LTD.

  公开号：EP0245662A1

  公开（公告）日：1987-11-19

  This invention is characterized by synthesizing an active ester represented by the general formula using an active esterifying agent consisting of a sulfonium salt represented by the general formula and further reacting the above-said active ester with a nucleophilic agent represented by the general formula H-B-Y to produce an ester or amide represented by the general formula (W)d A-B-Y, wherein A represents -CO-, -SO2-, >PO-, or >PS- groups; R, represents a hydrogen, an alkyl group, a halogen group, a nitro group, or an alkoxy group; R2 and R3, which may be same or different, each represents an alkyl group; X⊖ represents an anion typified by a halogen ion, a perchloric acid ion, a hydrogensulfuric acid ion, a methylsulfuric acid ion, and a p-toluenesulfonic acid ion; for W and d, when the above A is a divalent group, d is 1, and W represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkyl group of C1-C5 substituted by 1-3 halogen atoms, a group (wherein R4 and R5, which may be same or different, ead represents a hydrogen, a hydroxyl group, a mercapto group an alkyl group, or an aryl group; when Q is oxygen or sulfur, U is 0, and Re represents a hydrogen, an alkyl group, an ary group, a cycloalkyl group, an alkenyl group, an alkynyl group or an aralkyl group; when Q is nitrogen, u is 1, and R6 and R'6, which may be same or different, each represents a hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an aralkyl group; and k represents an integral number of 1-4), an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, an aralkoxy group represented by (wherein Rn represents a hydrogen, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an aryl group, or a group R7 and Rs, which may be same or different, each represents a hydrogen or an alkyl group; and m represents an integral number of 1-4), an isobonyloxy group, a furfuryloxy group, a fluorenylmethoxy group, or a group R9-R10N- (wherein R9 and R10, which may be same or different, each represents a hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an aralkyl group, or R9 and R10 may be combined each other to form a ring having 3-6 carbon atoms, when occasion demands, containing other hetero atoms), when the above A is particularly W may be an amino acid group in which a proper protective group is introduced or not Introduced in the α-amino group and/or the side chain together with W-Cl-, and/or a group or a peptide or protein, and ②when the above A is a trivalent group, d is 2 and, in this case, two Ws, which may be same or different, each represents an alkoxy group, an alkenoxy group, an alkyl group, an aralkoxy group, an aryloxy group, an alkylamino group, an alkylthio group, or an aryl group; B represents NR11 (wherein R11 represents a hydrogen, an alkyl group, an alkenyl group, an alkynyl group or an aryl groupl, oxygen, or sulfur ; and Y represents a group represented by (wherein Y represents a hdrogen, an alkyl group, a cycloalkyl group, a halogenoalkyl group, or an aryl group ; F represents NH, oxygen, sulfur alkylamino, or NHCO groups ; R12 and R13, which may be same or different, each represents a hydrogen, HO-, HS-, an alkyl group, an alkylthio group, an alkylamino group, an alkenyl group, an alkynyl group, or an aryl group, q is 0 or 1 ; and r represents an integral number of 0-4), or H-B-Y is an amino acid in which a proper protective group is introduced or not introduced in the side chain and/or the α-carboxyl group, a peptide or protein in which a proper protective group is introduced or not introduced in the side chain and/or the terminal carboxyl group, or a glucide in which the hydroxyl group in the molecule is properly protected or not protected.

  本发明的特点是通过使用由通式表示的锍盐组成的活性酯化剂合成通式表示的活性酯 使用由通式所代表的锍盐组成的活性酯化剂 并进一步将上述活性酯与通式 H-B-Y 所代表的亲核剂反应，生成通式 (W)d A-B-Y 所代表的酯或酰胺、 其中 A 代表-CO-、-SO2-、>PO-或>PS-基团；R 代表氢、烷基、卤素基团、硝基或烷氧基；R2 和 R3 可以相同或不同，各自代表烷基；X⊖ 代表卤素离子、高氯酸离子、氢硫酸离子、甲基硫酸离子和对甲苯磺酸离子等阴离子；对于 W 和 d、 当上述 A 为二价基团时，d 为 1，且 W 代表烷基、烯基、炔基、环烷基、被 1-3 个卤素原子取代的 C1-C5 烷基、基团 (其中 R4 和 R5 可以相同或不同，ead 代表氢、羟基、巯基、烷基或芳基；当 Q 为氧或硫时，U 为 0，Re 代表氢、烷基、芳基、环烷基、烯基、炔基或芳基；当 Q 为氮时，u 为 1，且 R6 和 R'6 可相同或不同，各自代表氢、烷基、烯基、炔基、芳基或芳烷基；且 k 代表 1-4 的整数）、烷氧基、环烷氧基、芳基、芳氧基、芳烷氧基，由以下各项代表的烷氧基 (其中 Rn 代表氢、卤素原子、烷基、烷氧基、烷硫基、烷基磺酰基、芳基或基团）。 R7 和 Rs 可以相同或不同，各自代表氢或烷基；和 m 代表 1-4 的整数）、异苯氧基基团、糠氧基基团、芴甲氧基基团或 R9-R10N- 基团（其中 R9 和 R10 可相同或不同，各自代表氢、烷基、烯基、炔基、芳基或芳烷基，或 R9 和 R10 可相互结合形成具有 3-6 个碳原子的环，当场合要求时，含有其他杂原子），当上述 A 特别是 W 可以是引入或未引入适当保护基团的氨基酸基团 在α-氨基基团和/或侧链中与 W-Cl- 一起引入，和/或一个基团或肽或蛋白质，以及 当上述 A 为三价基团时，d 为 2，在此情况下，两个 W（可以相同或不同）分别代表烷氧基、烯氧基、烷基、烷氧基、芳氧基、烷基氨基、烷硫基或芳基； B 代表 NR11（其中 R11 代表氢、烷基、烯基、炔基或芳基）、氧或硫；以及 Y 代表下列基团 (其中 Y 代表氢、烷基、环烷基、卤代烷基或芳基；F 代表 NH、氧、硫烷基氨基或 NHCO 基团；R12 和 R13 可以相同或不同，各自代表氢、HO-、HS-、烷基、烷硫基、烷基氨基、烯基、炔基或芳基；q 为 0 或 1；和 r 代表 0-4 的整数），或 H-B-Y 是在侧链和（或）α-羧基中引入或未引入适当保护基团的氨基酸、在侧链和（或）末端羧基中引入或未引入适当保护基团的肽或蛋白质，或分子中羟基受到或未受到适当保护的葡萄糖苷。
• Sulfonium compounds, as well as process for producing active esters and amides used for the production of amides
  申请人：SANSHIN KAGAKU KOGYO CO., LTD.

  公开号：EP0331988A1

  公开（公告）日：1989-09-13

  In the present invention an amide represented by the general formula: is produced using a sulfonium salt represented by the general formula: as the starting material, to synthesizing a novel compound, i.e., an active ester represented by the general formula: and further reacting the active ester with a nucleophilic agent represented by the general formula: H-B-Y wherein R1 represents a hydrogen, an alkyl group or a halogen group; R2 and R3, which may be same or different, each represents an alkyl group; X- represents an anion typified by a halogen ion, a perchloric acid ion, a hydrogen sulfuric acid ion, a methylsulfuric acid ion, and a p-toluenesulfonic acid ion; W represents an alkyl group, alkoxy group group, in which R4. represents a halogen, a hydrogen or a methoxy or a Ci - C5 alkyl group substituted with 1 - 3 halogen atoms, an aryl group or a fluorenylmethoxy group, or represents, together with W- C -, an amino acid, a peptide, or a protein group, in which the terminal amino group and the side chain group of the amino acid has or has not a protective group, B represents a substituted or not-substituted imino group, Y represents an organic group or B and Y join together to represent a heterocyclic amine. Alternatively H-BY represents an amino acid in which a proper protective group is or is not introduced into a-carboxyl group and/or side chain, or a peptide or protein in which a proper protective group is or is not introduced into the terminal carboxyl group and/or side chain.

  在本发明中，使用通式为 代表的酰胺作为起始原料，使用通式： 作为起始原料，合成一种新型化合物，即通式： 所代表的活性酯： 并进一步将该活性酯与通式： 所代表的亲核剂反应：H-B-Y 其中 R1 代表氢、烷基或卤素基团；R2 和 R3 可以相同或不同，各自代表烷基；X- 代表卤素离子、高氯酸离子、氢硫酸离子、甲硫 酸离子和对甲苯磺酸离子等类型的阴离子；W 代表烷基、烷氧基和烷烃基团。 其中 R4. 代表卤素、氢或甲氧基或被 1 - 3 个卤素原子取代的 Ci - C5 烷基、芳基或芴甲氧基，或与 W- C - 一起代表氨基酸、肽或蛋白质基团，其中 氨基酸的末端氨基和侧链基团具有或不具有保护基团；B 代表取代或未取代的亚氨基；Y 代表有机基团或 B 和 Y 连接在一起代表杂环胺。或者，H-BY 代表在羧基和/或侧链中引入或未引入适当保护基团的氨基酸，或在末端羧基和/或侧链中引入或未引入适当保护基团的肽或蛋白质。
• OKAI, XIDEHO
  作者：OKAI, XIDEHO

  DOI：——

  日期：——
• US4857656A
  申请人：——

  公开号：US4857656A

  公开（公告）日：1989-08-15
• US5117031A
  申请人：——

  公开号：US5117031A

  公开（公告）日：1992-05-26