(S)-[5-Amino-1-(methoxy-methyl-carbamoyl)-pentyl]carbamic acid tert-butyl ester | 201006-45-3

• 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)-[5-Amino-1-(methoxy-methyl-carbamoyl)-pentyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-6-amino-1-[methoxy(methyl)amino]-1-oxohexan-2-yl]carbamate
• CAS: 201006-45-3
• 化学式: C₁₃H₂₇N₃O₄
• 分子量: 289.375
• InChiKey: JGJSNLJWLYLIJR-JTQLQIEISA-N

物化性质

• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-[5-Amino-1-(methoxy-methyl-carbamoyl)-pentyl]carbamic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl N-[(E,3S)-7-amino-1-(benzenesulfonyl)hept-1-en-3-yl]carbamate
  参考文献：
  名称：

  乙烯基砜是基于机理的半胱氨酸蛋白酶抑制剂。

  摘要：

  DOI：

  10.1021/jm00017a002
• 作为产物：
  描述：

  Boc-Lys(Cbz)-(N-Me)OMe 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以97%的产率得到(S)-[5-Amino-1-(methoxy-methyl-carbamoyl)-pentyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides

  摘要：

  The solvatochromic IR responsivity of small side chain-NCS in two unexplored unnatural amino acids, isothiocyanyl alanine ((NCS)Ala = Ita) and lysine ((NCS)Lys = Itl), without perturbing the conformation is demonstrated in two designed short tripeptide (BocAla-(NCS)Ala-Ala-OMe) and hexapeptide (BocLeu-ValPhe- Phe-(NCS)Lys-Gly-OMe). Demonstration of site specific fluorescent labeling in both the peptides and ligation type reaction in (NCS)Lys indicates the novelty of these two amino acids as alternative to the available canonical amino acids. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2018.02.021

文献信息

• Intramolecular cyclization of isothiocyanyl amino acids/peptide: arrival at unnatural thioxoimidazolidinyl/thioxooxazolidinyl amino acids
  作者：Subhendu Sekhar Bag、Suranjan De、Shilpa Bhuyan

  DOI：10.1007/s00726-022-03186-w

  日期：2022.11

  A novel intramolecular cyclization of isothiocyanyl amino acids/peptide is reported to arrive at unnatural thioxoimidazolidinyl (TOI)/thioxooxazolidinyl (TOO) amino acids for the first time. Interestingly, analogous isothiocyanyl amines under a similar reaction condition either follow 5-endo-dig cyclization to offer 5-membered thiourea or acyclic diethylaminyl thiourea derivative instead of 6-membered

  据报道，异硫氰基氨基酸/肽的新型分子内环化首次达到非天然硫代咪唑烷基 (TOI)/硫代恶唑烷基 (TOO) 氨基酸。有趣的是，在相似的反应条件下，类似的异硫氰基胺要么遵循 5-endo-dig 环化，要么提供 5 元硫脲或无环二乙氨基硫脲衍生物，而不是 6 元环状硫脲。
• Potent and selective bicyclic lactam inhibitors of thrombin: Part 3: P1′ modifications
  作者：Janet S. Plummer、Kent A. Berryman、Cuiman Cai、Wayne L. Cody、John DiMaio、Annette M. Doherty、Scott Eaton、Jeremy J. Edmunds、Debra R. Holland、D. Lafleur、Sophie Levesque、Lakshmi S. Narasimhan、J.Ronald Rubin、Stephen T. Rapundalo、M.Arshad Siddiqui、A. Susser、Yves St-Denis、Peter Winocour

  DOI：10.1016/s0960-894x(99)00096-7

  日期：1999.3

  The synthesis and antithrombotic activity of a series of nonpeptide bicyclic thrombin inhibitors are described. We have explored the SAR around the P1' site. Modification of the P1' site has been found to affect potency and selectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Fantetti, Lia; Adembri, Giorgio; Giotti, Alberto, Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 2, p. 137 - 143
  作者：Fantetti, Lia、Adembri, Giorgio、Giotti, Alberto、Masini, Ilaria、Roncucci, Gabrio

  DOI：——

  日期：——
• US6291678B1
  申请人：——

  公开号：US6291678B1

  公开（公告）日：2001-09-18
• Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides
  作者：Subhendu Sekhar Bag、Suranjan De

  DOI：10.1016/j.bmcl.2018.02.021

  日期：2018.5

  The solvatochromic IR responsivity of small side chain-NCS in two unexplored unnatural amino acids, isothiocyanyl alanine ((NCS)Ala = Ita) and lysine ((NCS)Lys = Itl), without perturbing the conformation is demonstrated in two designed short tripeptide (BocAla-(NCS)Ala-Ala-OMe) and hexapeptide (BocLeu-ValPhe- Phe-(NCS)Lys-Gly-OMe). Demonstration of site specific fluorescent labeling in both the peptides and ligation type reaction in (NCS)Lys indicates the novelty of these two amino acids as alternative to the available canonical amino acids. (C) 2018 Published by Elsevier Ltd.