N-[(1,1-二甲基乙氧基)羰基]-L-蛋氨酸 4-硝基苯基酯 | 2488-18-8

• 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: N-[(1,1-二甲基乙氧基)羰基]-L-蛋氨酸 4-硝基苯基酯
• 中文别名: N-[(1,1-二甲基乙氧基)羰基]-L-蛋氨酸4-硝基苯基酯；BOC-L-蛋氨酸-对硝基苯酯
• 英文名称: N-((tert-butyloxy)carbonyl)-L-methionine p-nitrophenyl ester
• 英文别名: (tert-butyloxycarbonyl)-L-methionine p-nitrophenyl ester；N-tert-butyloxycarbonyl-L-methionine p-nitrophenyl ester；tert-butyloxycarbonyl-L-methionine p-nitrophenyl ester；N-tert-butoxycarbonylmethionine p-nitrophenyl ester；tert-butoxycarbonyl-L-methionine p-nitrophenylester；N-tBoc-L-methionine 4-nitrophenyl este；Boc-Met-ONp；(4-nitrophenyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoate
• CAS: 2488-18-8
• 化学式: C₁₆H₂₂N₂O₆S
• mdl: MFCD00038123
• 分子量: 370.426
• InChiKey: KSFQSYDCSRCMIR-ZDUSSCGKSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  536.1±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 储存条件：
  室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  N-[(1,1-二甲基乙氧基)羰基]-L-蛋氨酸 4-硝基苯基酯 在 (S)-chloro(1-phenylethanamine-C,N)-(pyridine)palladium(II) 作用下， 以 phosphate buffer 为溶剂， 生成 Boc-L-蛋氨酸
  参考文献：
  名称：

  Catalytic hydrolysis of α-amino esters in the presence of chiral palladacycles

  摘要：

  The rate of hydrolysis of esters derived from optically active alpha-amino acids, catalyzed by chiral cyclopalladated benzylamines, depends on the configuration of chiral centers in the substrate and catalyst. The catalytic hydrolysis of sulfur-containing amino esters follows an intramolecular mechanism, and the difference in the reaction rates for the stereoisomers increases in going from ortho-palladated primary benzylamines (k(S)/k(R) = 1.1) to tertiary amines (k(S)/k(R) = 1.5); the strongest catalytic effect is observed for an ester and a complex with the same absolute configuration of the chiral centers. The efficiency of intermolecular catalysis is greater for a complex and ester with opposite absolute configurations of the chiral centers, and the rate constants of catalytic hydrolysis for two pairs of stereoisomers coincide within experimental error. The maximal difference in the reaction rates is observed for cyclopalladated secondary benzylamines; it reaches 2.3 for the phenylalanine ester.

  DOI：

  10.1134/s1070428007040100
• 作为产物：
  描述：

  L-蛋氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 为溶剂， 生成 N-[(1,1-二甲基乙氧基)羰基]-L-蛋氨酸 4-硝基苯基酯
  参考文献：
  名称：

  多肽的研究。XXXI。与牛胰腺核糖核酸酶N位点有关的合成肽（位置12-20）。

  摘要：

  DOI：

  10.1021/ja01081a041

文献信息

• Amino acids and peptides. XXI. Synthesis of N-terminal heptapeptide of mammalian metallothionein(MT) and evaluation of its immunoreactivity.
  作者：YOSHIO OKADA、SHIN IGUCHI、SHIGERU NAKAYAMA、YUTAKA KIKUCHI、MASACHIKA IRIE、JUN-ICHI SAWADA、HIDEHARU IKEBUCHI、TADAO TERAO

  DOI：10.1248/cpb.36.3614

  日期：——

  The common N-terminal heptapeptide, Ac-Met-Asp-Pro-Asn-Cys-Ser-Cys-OH, Ac-(MT II 1-7)-OH, of mammalian metallothioneins (MTs) was synthesised by a conventional solution method using newly developed β-2-adamantylasparate. This peptide was as reactive as native MT with a monoclonal antibody produced against rat Zn-MT II.

  哺乳动物金属硫蛋白（MTs）的共同N端七肽Ac-Met-Asp-Pro-Asn-Cys-Ser-Cys-OH，即Ac-(MT II 1-7)-OH，通过使用新开发的β-2-金刚烷基天冬氨酸，采用传统的溶液方法合成。该肽与针对大鼠Zn-MT II产生的单克隆抗体同样具有反应性。
• N-benzhydryl-glycolamide esters (OBg esters) as carboxyl protecting groups in pept1de synthesis
  作者：Muriel Amblard、Marc Rodriguez、Jean Martinez

  DOI：10.1016/s0040-4020(01)86014-2

  日期：1988.1

  N-Benzhydryl-glycolamide esters (OBg esters) of various N-protected amino acids have been synthesized. In order to demonstrate their usefulness in peptide chemistry, the syntheses of For-Met-Leu-Phe-OH (chemiotactic peptide) and Pro-Leu-Gly-NH2 (MIF) have been carried out. OBg esters are compatible with commonly used protecting groups and are cleanly and selectively removed in mild alkaline conditions

  已经合成了各种N-保护的氨基酸的N-苯甲酰基-乙醇酰胺酯（OBg酯）。为了证明它们在肽化学中的有用性，已经进行了For-Met-Leu-Phe-OH（趋化肽）和Pro-Leu-Gly-NH 2（MIF）的合成。OBg酯与常用的保护基团相容，并且除含有β-苄基天冬氨酰的序列外，在温和的碱性条件下可以干净而有选择地除去，而没有任何副反应。
• Synthesis of the heptadecapeptide corresponding to the entire amino acid sequence of salmon melanin-concentrating hormone (MCH).
  作者：KENJI OKAMOTO、KOICHI YASUMURA、KAZUYOSHI FUJITANI、YOSHIAKI KISO、HIROSHI KAWAUCHI、ICHIRO KAWAZOE、HARUAKI YAJIMA

  DOI：10.1248/cpb.32.2963

  日期：——

  The heptadecapeptide corresponding to the entire amino acid sequence of melaninconcentrating hormone (MCH), isolated from chum salmon pituitaries, was synthesized by successive condensation of four peptide fragments and the N-terminal amino acid, i. e., Boc-(14-17)-OBzl, Boc-(9-13)-OH, Boc-(5-8)-NHNH2, Boc-(2-4)-NHNH2 and Boc-Asp (OBzl)-OH, followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid (TFA) and disulfide formation through the S-sulfonate. When melanin-concentrating activity was measured on a tilapia scale, the minimum effective concentration of the synthetic peptide was equivalent to that of natural salmon MCH (1nM).

  从大麻哈鱼脑下垂体中分离出的、与促黑激素（MCH）整个氨基酸序列相对应的十七肽，是通过四个肽片段和N-端氨基酸，即Boc-(14-17)-OBzl、Boc-(9-13)-OH、Boc-(5-8)-NHNH2、Boc-(2-4)-NHNH2 和Boc-Asp(OBzl)-OH，依次缩合合成，随后用三氟乙酸（TFA）中的1M三氟甲磺酸-硫茴处理，通过S-磺酸酯形成二硫键并去保护。当在罗非鱼身上测量促黑活性时，合成肽的最小有效浓度与天然大麻哈鱼MCH的浓度（1nM）相当。
• Synthesis of a tetradecapeptide corresponding to sequence 90-103 of bovine adrenodoxin.
  作者：KOICHI KAWASAKI、CHIYE KAWASAKI、MITSUKO MAEDA、YOSHIO OKADA

  DOI：10.1248/cpb.28.2105

  日期：——

  Two tetradecapeptides, Z-Leu-Gly-Cys (Bzl)-Gln-Ile-Cys (Bzl)-Leu-Thr-Lys (Z)-Ala-Met-Asp (OBzl)-Asn-Met-OH (I) and its benzyl ester (VIII) were synthesized. I was synthesized by the condensation of two heptapeptides [Z-Leu-Gly-Cys (Bzl)-Gln-Ile-Cys (Bzl)-Leu-NHNH2 (II) and Boc-Thr-Lys (Z)-Ala-Met-Asp (OBzl)-Asn-Met-OH (III)], while VIII was synthesized stepwise by the condensation of 4 fragments [Z-Leu-Gly-Cys (Bzl)-Gln-OH (XI), Boc-Ile-Cys (Bzl)-Leu-OH (X), Boc-Thr-Lys (Z)-Ala-NHNH2 (IV) and Boc-Met-Asp (OBzl)-Asn-Met-OBzl (IX)]. Deblocked I and deblocked VIII each formed a chelate with iron and sulfur.

  合成了两个十四肽，Z-Leu-Gly-Cys（Bzl）-Gln-Ile-Cys（Bzl）-Leu-Thr-Lys（Z）-Ala-Met-Asp（OBzl）-Asn-Met-OH（I）及其苄酯（VIII）。I是通过两个七肽[Z-Leu-Gly-Cys（Bzl）-Gln-Ile-Cys（Bzl）-Leu-NHNH2（II）和Boc-Thr-Lys（Z）-Ala-Met-Asp（OBzl）-Asn-Met-OH（III）]的缩合合成的，而VIII则是通过4个片段[Z-Leu-Gly-Cys（Bzl）-Gln-OH（XI），Boc-Ile-Cys（Bzl）-Leu-OH（X），Boc-Thr-Lys（Z）-Ala-NHNH2（IV）和Boc-Met-Asp（OBzl）-Asn-Met-OBzl（IX）]的逐步缩合合成的。去保护后的I和去保护后的VIII分别与铁和硫形成了配合物。
• Amino acids and peptides. XVII. Synthesis of a tridecapeptide corresponding to the sequence 165-177 of T-kininogen (tryptic peptide) containing Gln-Val-Val-Ala-Gly sequence and the relationship between structure and effect on thiol proteinase.
  作者：NAOKI TENO、SATOSHI TSUBOI、YOSHIO OKADA、NORIO ITOH、HIROSHI OKAMOTO

  DOI：10.1248/cpb.35.3853

  日期：——

  The tridecapeptide corresponding to the sequence 165-177 of T-kininogen (tryptic peptide) (I) containing Gln-Val-Val-Ala-Gly sequence was synthesized by a conventional solution method and its effect on thiol proteinase was examined. Although Z-Gln-Val-Val-Ala-Gly-OMe showed inhibitory activity towards papain and protective activity against T-kininogen-induced inhibition of papain, the tryptic peptide obtained did not exhibit any effect on thiol proteinase. In order to study the relationship between structure and effect on thiol proteinase, several compounds (II-VI) modified with various groups at the N-terminus of the Gln-Val-Val-Ala-Gly sequence were synthesized. Peptides V and VI, which have an aromatic ring at the N-terminus, exhibited weak inhibitory and significant protective activities. A small peptide such as Gln-Val-Val-Ala-Gly might be better able to approach papain than the tryptic peptide (I), and the aromatic ring associated with Gln-Val-Val-Ala-Gly at the N-terminus apparently strengthened the binding ability of the peptide to papain.

  与T-激肽原（胰蛋白酶肽）序列165-177对应的三肽（I），含有Gln-Val-Val-Ala-Gly序列，通过传统溶液法合成，并对其对巯基蛋白酶的作用进行了研究。尽管Z-Gln-Val-Val-Ala-Gly-OMe对木瓜蛋白酶表现出抑制活性，并能保护木瓜蛋白酶免受T-激肽原诱导的抑制，但所获得的胰蛋白酶肽对巯基蛋白酶没有任何作用。为了研究结构与对巯基蛋白酶作用之间的关系，合成了几种在Gln-Val-Val-Ala-Gly序列的N-末端修改了不同基团的化合物（II-VI）。具有芳香环的肽V和VI表现出弱抑制和显著保护活性。像Gln-Val-Val-Ala-Gly这样的小肽可能比肽（I）更容易接近木瓜蛋白酶，而Gln-Val-Val-Ala-Gly N-末端的芳香环显然增强了肽与木瓜蛋白酶的结合能力。