N'-对甲苯磺酰基-L-精氨酸 | 4353-32-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 精氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N'-对甲苯磺酰基-L-精氨酸
• 英文名称: H-L-Arg(Tos)-OH
• 英文别名: H-Arg(Tos)-OH；(2S)-5-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]-2-azaniumylpentanoate
• CAS: 4353-32-6
• 化学式: C₁₃H₂₀N₄O₄S
• mdl: MFCD00077167
• 分子量: 328.392
• InChiKey: SLTWQHUEZWYAOI-NSHDSACASA-N

物化性质

• 熔点：
  146-150 °C
• 沸点：
  528.3±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  156
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2935009090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N'-对甲苯磺酰基-L-精氨酸 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 甲酸 、 氢气 、 sodium cyanoborohydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 2-甲基-2-丁醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.5h， 生成 (N^α-Me)Arg(Tos)-Gly-Asp(O-cHex)-Man(4-MeBzl)
  参考文献：
  名称：

  Ali; Bennett; Calvo, Journal of Medicinal Chemistry, 1994, vol. 37, # 6, p. 769 - 780

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-L-精氨酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 26.0h， 生成 N'-对甲苯磺酰基-L-精氨酸
  参考文献：
  名称：

  The discovery, characterization and crystallographically determined binding mode of an FMOC-containing inhibitor of HIV-1 protease

  摘要：

  A pharmacophore derived from the structure of the dithiolane derivative of haloperidol bound in the active site of the HIV-1 protease (HIV-1 PR) has been used to search a three-dimensional database for new inhibitory frameworks. This search identified an FMOC-protected N-tosyl arginine as a lead candidate. A derivative in which the arginine carboxyl has been converted to an amide has been crystallized with HIV-1 PR and the structure has been determined to a resolution of 2.5 Angstrom with a final R-factor of 18.5%. The inhibitor binds in an extended conformation that results in occupancy of the S2, S1', and S3' subsites of the active site. Initial structure-activity studies indicate that: (1) the FMOC fluorenyl moiety interacts closely with active site residues and is important for binding; (2) the N-G-tosyl group is necessary to suppress protonation of the arginine guanidinyl terminus; and (3) the arginine carboxamide function is involved in interactions with the water coordinated to the catalytic aspartyl groups. FMOC-protected arginine derivatives, which appear to be relatively specific and nontoxic, offer promise for the development of useful HIV-1 protease inhibitors. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00078-3

文献信息

• Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids
  作者：Nicolai Stuhr-Hansen、Shahrokh Padrah、Kristian Strømgaard

  DOI：10.1016/j.tetlet.2014.05.090

  日期：2014.7

  procedure is developed for the synthesis of α-hydroxy carboxylic acids by treatment of the corresponding protonated α-amino acid with tert-butyl nitrite in 1,4-dioxane–water. The amino moiety must be protonated and located α to a carboxylic acid function in order to undergo initial diazotization and successive hydroxylation, since neither β-amino acids nor acid derivatives such as esters and amides undergo

  通过在1,4-二恶烷-水中用亚硝酸叔丁酯处理相应的质子化α-氨基酸，开发了一种有效且改进的合成α-羟基羧酸的方法。由于β-氨基酸或酸衍生物（如酯和酰胺）均不会发生羟基化作用，因此必须对氨基部分进行质子化并将α定位于羧酸官能团，以便进行初始重氮化和连续的羟基化作用。该方法已成功应用于18种蛋白氨基酸的合成。
• Synthesis of Silacyclic Dipeptides: Peptide Elongation at Both N- and C-Termini of Dipeptide
  作者：Tomohiro Hattori、Hisashi Yamamoto

  DOI：10.1021/jacs.1c11260

  日期：2022.2.2

  A new type of peptide bond formation utilizing silacyclic amino acids or peptides is described. This work has the following advantages: (1) imidazolylsilane is a highly fascinating coupling reagent for dipeptide synthesis from N-,C-terminal unprotected amino acids with amino acid tert-butyl esters; (2) deprotection of the tert-butyl ester at the C-terminus and cyclization sequentially proceed depending

  描述了一种利用硅环氨基酸或肽形成的新型肽键。该工作具有以下优点： (1) 咪唑基硅烷是一种极具吸引力的偶联剂，可用于从 N-、C-末端未保护的氨基酸与氨基酸叔丁酯合成二肽；(2)叔的去保护C末端的-丁酯和环化根据反应条件依次进行，得到新的硅环二肽；(3)环化产物显示出作为肽延伸底物的显着能力，因为硅环化合物可以作为亲核试剂和亲电子试剂，并且这种能力导致一锅位点选择性四肽和寡肽合成。这些创新优势将有助于显着简化经典肽合成。
• Studies on Peptides. XLIII. Synthesis of Two Protected Peptides Related to the C-Terminal Portion of the Basic Trypsin Inhibitor from Bovine Pancreas (Kunitz and Northrop)
  作者：HARUAKI YAJIMA、YOSHIAKI KISO、KOUKI KITAGAWA

  DOI：10.1248/cpb.22.1079

  日期：——

  The protected nonadecapeptide and the C-terminal dipeptide corresponding to positions 38 through 56 and 57-58 of the basic trypsin inhibitor from bovine pancreas were prepared. Synthesis of the protected nonadecapeptide, Z (OMe)-Cys (Bzl)-Arg (Tos)-Ala-Lys (Z)-Arg (Tos)-Asn-Asn-Phe-Lys (Z)-Ser-Ala-Glu (OBzl)-Asp (OBzl)-Cys (Bzl)-Met-Arg (Tos)-Thr-Cys (Bzl)-Gly-OH, was achieved by condensation of three subunits : Z (OMe)-Cys (Bzl)-Arg (Tos)-Ala-Lys (Z)-Arg (Tos)-NHNH2 (positions 38-42), Z (OMe)-Asn-Asn-Phe-Lys (Z)-Ser-Ala-NHNH2 (positions 43-48) and Z (OMe)-Glu (OBzl)-Asp (OBzl)-Cys (Bzl)-Met-Arg (Tos)-Thr-Cys (Bzl)-Gly-OH (positions 49-56). The C-terminal dipeptide was prepared in a form of Z (OMe)-Gly-Ala-OH.

  制备了对应于来自牛胰腺的碱性胰蛋白酶抑制剂的38至56和57-58位的受保护的九肽和C端二肽。受保护的九肽 Z (OMe)-Cys (Bzl)-Arg (Tos)-Ala-Lys (Z)-Arg (Tos)-Asn-Asn-Phe-Lys (Z)-Ser-Ala-Glu 的合成（ OBzl)-Asp (OBzl)-Cys (Bzl)-Met-Arg (Tos)-Thr-Cys (Bzl)-Gly-OH，通过三个亚基缩合获得：Z (OMe)-Cys (Bzl)-Arg (Tos)-Ala-Lys (Z)-Arg (Tos)-NHNH2（位置 38-42），Z (OMe)-Asn-Asn-Phe-Lys (Z)-Ser-Ala-NHNH2（位置 43-48） )和Z(OMe)-Glu(OBzl)-Asp(OBzl)-Cys(Bzl)-Met-Arg(Tos)-Thr-Cys(Bzl)-Gly-OH(位置49-56)。 C端二肽以Z(OMe)-Gly-Ala-OH的形式制备。
• Synthesis and analgesic activity of neo-kyotorphin analogs.
  作者：KOUKI KITAGAWA、NOBUYUKI KAWAI、SHINYA KIYAMA、TADASHI AKITA、YOSHIAKI KISO、HIROSHI UEDA、MING GE、HIROSHI TAKAGI

  DOI：10.1248/cpb.33.377

  日期：——

  Seven analogs which contain D-amino acids or the sterically hindered amino acid Pro, and two short-chain analogs of neo-kyotorphin (1), an analgesic pentapeptide isolated from bovine brain, were synthesized by the conventional method and screened for analgesic activity. All the analogs exhibited significantly enhanced analgesic effect upon intracisternal administration in mice. In particular, [D-Ser2]-and [Pro2]-neo-kyotorphin exhibited almost 10 times more potent activity than neo-kyotorphin.

  采用传统方法合成了七种含有 D-氨基酸或立体受阻氨基酸 Pro 的类似物，以及从牛脑中分离出的镇痛五肽--新基吗啡（1）的两种短链类似物，并对其镇痛活性进行了筛选。所有类似物在小鼠鞘内给药时都表现出明显增强的镇痛效果。其中，[D-Ser2]-和[Pro2]-新基吗啡的活性几乎是新基吗啡的 10 倍。
• Synthesis and activity of a newly isolated analgesic pentapeptide, neo-kyotorphin.
  作者：KOUKI KITAGAWA、NOBUYUKI KAWAI、YOSHIAKI KISO、TADASHI AKITA、KIYOSHI FUKUI、HIROO AMANO、HIROSHI TAKAGI

  DOI：10.1248/cpb.31.2349

  日期：——

  A newly isolated bovine brain pentapeptide, Thr-Ser-Lys-Tyr-Arg (neo-kyotorphin), which contains the Tyr-Arg (kyotorphin) unit at its carboxyl terminal portion, was synthesized by using the TFMSA-TFA-thioanisole deprotecting procedure. The synthetic peptide exhibited dosedependent analgesic activity in mice at a level approximately equal to that of Leu-enkephalin.

  采用 TFMSA-TFA-thioanisole 去保护程序合成了一种新分离的牛脑五肽 Thr-Ser-Lys-Tyr-Arg（新基吗啡），其羧基末端部分含有 Tyr-Arg（基吗啡）单元。合成肽在小鼠体内表现出剂量依赖性镇痛活性，其水平与亮啡肽（Leu-enkephalin）大致相同。