Boc-Phe-ψ(CH2NH)-Gly-OMe | 128421-95-4

• 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: Boc-Phe-ψ(CH2NH)-Gly-OMe
• 英文别名: methyl 2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropyl]amino]acetate
• CAS: 128421-95-4
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: JYUFZHQMDNOHIK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  胸腺嘧啶-1-乙酸 、 Boc-Phe-ψ(CH2NH)-Gly-OMe 在 TEA 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl N-(2-Boc-amino-3-phenylpropyl)-N-(thymin-1-ylacetyl)glycinate
  参考文献：
  名称：

  Synthesis of New Chiral Peptide Nucleic Acid (PNA) Monomers by a Simplified Reductive Animation Method

  摘要：

  The aim of this work was the preparation of four new peptide nucleic acid (PNA) monomer backbone by reductive amination of N-alpha-Boc-protected chiral amino aldehydes, derived from Leu, Phe, Tyr(Bzl), and Thr(Bzl), with methyl glycinate. To the crude 2-substituted methyl N-(2-Boc-aminoethyl)glycinates obtained, thymin-1-ylacetic acid was coupled using TBTU procedure in a one-pot reaction. PNA monomers were isolated and characterized.

  DOI：

  10.1080/15257779908043081
• 作为产物：
  描述：

  [((S)-2-tert-Butoxycarbonylamino-3-phenyl-propyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester 在 potassium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 以81%的产率得到Boc-Phe-ψ(CH2NH)-Gly-OMe
  参考文献：
  名称：

  Synthesis of achiral and chiral peptide nucleic acid (PNA) monomers using Mitsunobu reaction

  摘要：

  Peptide nucleic acids (PNAs) are intensively studied DNA analogues. We elaborated an efficient procedure for the synthesis of N-, C-protected pseudodipeptides with a reduced peptide bond and then peptide nucleic acid (PNA) monomers, based on the Mitsunobu reaction of N-Boc-beta -amino alcohols with N-o-nitrobenzenesulfonyl-protected (oNBS-protected) amino acid esters. Using the new procedure, we obtained protected PNA monomer backbones with various amino acid side chains. The pseudodipeptide, secondary amine groups were then deprotected by thiolysis, and after appropriate work-up, acylated with thymin-1-ylacetic acid to give the protected monomers. The procedure seems to be of general applicability and allows various modifications of PNA structure by using diverse alcohols and amino acid esters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00759-1

文献信息

• An improved method for the preparation of desoxopeffides—reductions of endothiopeptides
  作者：Frank S. Guziec、Loide Mayer Wasmund

  DOI：10.1016/s0040-4039(00)94324-7

  日期：1990.1

  Three new procedures for the synthesis of desoxopeptides from endothiopeptides are reported: 1) Raney nickel desulfurizafion, 2) alkylation with triethyloxonium tetrafluoroborate followed by sodium borohydride reduction, and 3) nickel boride reduction. Of these three, reduction with nickel boride was found to be superior due to high yields, reproducibility and convenience.

  从内硫肽合成脱氧肽的三种新方法已有报道：1）阮内镍脱​​硫基硫脲； 2）四氟硼酸三乙基氧鎓烷基化，然后硼氢化钠还原； 3）硼化镍还原。在这三种方法中，由于高收率，可重复性和便利性，发现用硼化镍还原效果更好。