(S)-methyl 2-(2-(tert-butoxycarbonylamino)hexanamido)acetate | 114516-71-1

• 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: (S)-methyl 2-(2-(tert-butoxycarbonylamino)hexanamido)acetate
• 英文别名: Boc-Nle-Gly-OMe；methyl 2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]acetate
• CAS: 114516-71-1
• 化学式: C₁₄H₂₆N₂O₅
• 分子量: 302.371
• InChiKey: UJQXFVZSVNMXIA-JTQLQIEISA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  445.3±25.0 °C(predicted)
• 密度：
  1.073±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(2-(tert-butoxycarbonylamino)hexanamido)acetate 在 phosphate buffer 、 Bacillus subtilis esterase 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 48.0h， 以87%的产率得到N-tert-butyloxycarbonyl-norleucyl-glycine
  参考文献：
  名称：

  酶去除羧基保护基。2.裂解苄基和甲基部分

  摘要：

  酶是用于有效去除甲基和苄基保护基团的通用试剂。来自枯草芽孢杆菌的酯酶（BS2）和来自南极假丝酵母的脂肪酶（CAL-A）可以高产率温和而选择性地除去这些部分，而不会影响其他官能团。

  DOI：

  10.1021/jo051004v
• 作为产物：
  描述：

  甘氨酸甲酯盐酸盐 、 N-Boc-L-正亮氨酸 在 N-甲基吗啉 、 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 生成 (S)-methyl 2-(2-(tert-butoxycarbonylamino)hexanamido)acetate
  参考文献：
  名称：

  Peptide and pseudopeptide analogues of cholecystokinin, chemical modifications of the met28-gly29 region

  摘要：

  DOI：

  10.1016/s0040-4020(01)86144-5

文献信息

• Synthesis and Biological Evaluation of Potent, Selective, Hexapeptide CCK-A Agonist Anorectic Agents
  作者：M. Edward Pierson、Jeanne M. Comstock、Roy D. Simmons、Frederick Kaiser、Ronald Julien、John Zongrone、James D. Rosamond

  DOI：10.1021/jm970477u

  日期：1997.12.1

  Cholecystokinin (CCK) is a 33-amino acid peptide with multiple functions in both the central nervous system (via CCK-B receptors) and the periphery (via CCK-A receptors). CCK mediation of satiety via the A-receptor subtype suggest a role for CCK in the management of obesity. The carboxy terminal octapeptide (CCK-8) is fully active in this regard, but is lacking in receptor selectivity, metabolic stability, and oral bioavailability. Inversion of the chirality of Asp(7) in conjunction with N-methylation of Phe(8) produces compound 5 which exhibits high affinity and 2100-fold selectivity for CCK-A receptors. Compound 6 (Hpa(SO3H)-Me-Gly-Trp-Nle-MeAsp-Phe-NH2), derived from moving the N-methyl group from Phe to Asp, decreased CCK-B affinity substantially without affecting CCK-A affinity, giving a compound with 6600-fold selectivity for CCK-A receptors. These compounds inhibit food intake with nanomolar potency following intraperitoneal administration in fasted rats. In addition to greater potency, compound 6 produces weight loss in rats when administered over nine consecutive days. Intranasal administration of 6 potently inhibits feeding in beagle dogs. Compound 6 produces potent anorectic activity via the CCK-A receptor system.
• 2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides
  作者：Efrosini Barbayianni、Daren Stephens、Andrej Grkovich、Victoria Magrioti、Yuan-Hao Hsu、Panagiotis Dolatzas、Dimitrios Kalogiannidis、Edward A. Dennis、George Kokotos

  DOI：10.1016/j.bmc.2009.03.069

  日期：2009.7

  A series of 2-oxoamides based on dipeptides and pseudodipeptides were synthesized and their activities towards two human intracellular phospholipases A(2) (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase A(2) (GV sPLA(2)) were evaluated. Derivatives containing a free carboxyl group are selective GIVA cPLA(2) inhibitors. A derivative based on the ethyl ester of an ether pseudodipeptide is the first 2-oxoamide, which preferentially inhibits GVIA iPLA2. The effect of 2-oxoamides on the generation of arachidonic acid from RAW 264.7 macrophages was also studied and it was found that selective GIVA cPLA(2) inhibitors preferentially inhibited cellular arachidonic acid release; one pseudodipeptide gave an IC50 value of 2 mu M. (C) 2009 Elsevier Ltd. All rights reserved.
• YAUTI, XARAMASU;SUGIURA, NOBUO
  作者：YAUTI, XARAMASU、SUGIURA, NOBUO

  DOI：——

  日期：——
• MENDRE, C.;RODRIGUEZ, M.;LAUR, J.;AUMELAS, A.;MARTINEZ, J., TETRAHEDRON, 44,(1988) N 14, C. 4415-4430
  作者：MENDRE, C.、RODRIGUEZ, M.、LAUR, J.、AUMELAS, A.、MARTINEZ, J.

  DOI：——

  日期：——