(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

• Peptide and pseudopeptide analogues of cholecystokinin, chemical modifications of the met28-gly29 region
  作者：C. Mendre、M. Rodriguez、J. Laur、A. Aumelas、J. Martinez

  DOI：10.1016/s0040-4020(01)86144-5

  日期：1988.1
• 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.
• 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：——
• Enzymatic Removal of Carboxyl Protecting Groups. 2. Cleavage of the Benzyl and Methyl Moieties
  作者：Efrosini Barbayianni、Irene Fotakopoulou、Marlen Schmidt、Violetta Constantinou-Kokotou、Uwe T. Bornscheuer、George Kokotos

  DOI：10.1021/jo051004v

  日期：2005.10.1

  Enzymes are versatile reagents for the efficient removal of methyl and benzyl protecting groups. An esterase from Bacillus subtilis (BS2) and a lipase from Candida antarctica (CAL-A) allow a mild and selective removal of these moieties in high yields without affecting other functional groups.

  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。