N-(9-fluorenylmethoxycarbonyl)-Nⁱ-(butoxycarbonyl)-L-tryptophanyl-L-prolyl-O-(tert-butyl)-L-aspartyl-glycine tert-butyl ester | 475101-73-6

• 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: N-(9-fluorenylmethoxycarbonyl)-Nⁱ-(butoxycarbonyl)-L-tryptophanyl-L-prolyl-O-(tert-butyl)-L-aspartyl-glycine tert-butyl ester
• 英文别名: Fmoc-Trp(Boc)-Pro-Asp(OtBu)-Gly-OtBu；tert-butyl 3-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2S)-2-[[(2S)-4-[(2-methylpropan-2-yl)oxy]-1-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-1,4-dioxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-oxopropyl]indole-1-carboxylate
• CAS: 475101-73-6
• 化学式: C₅₀H₆₁N₅O₁₁
• 分子量: 908.061
• InChiKey: RMMZZQRMLDBUNP-ZHTZQEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  66
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  201
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-Nⁱ-(butoxycarbonyl)-L-tryptophanyl-L-prolyl-O-(tert-butyl)-L-aspartyl-glycine tert-butyl ester 在 吗啉 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到H-Trp(Boc)-Pro-Asp(OtBu)-Gly-OtBu
  参考文献：
  名称：

  Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin

  摘要：

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00327-x
• 作为产物：
  描述：

  甘氨酸叔丁酯 在 palladium on activated charcoal WCSD*HCl 、 氢气 、 1-羟基苯并三唑 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-(9-fluorenylmethoxycarbonyl)-Nⁱ-(butoxycarbonyl)-L-tryptophanyl-L-prolyl-O-(tert-butyl)-L-aspartyl-glycine tert-butyl ester
  参考文献：
  名称：

  Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin

  摘要：

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00327-x

文献信息

• Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase
  作者：Jun‐ichi Tamura、Akihiro Yamaguchi、Junko Tanaka、Yuko Nishimura

  DOI：10.1080/07328300701296810

  日期：2007.4.30

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.
• Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin
  作者：Jun-ichi Tamura、Akihiro Yamaguchi、Junko Tanaka

  DOI：10.1016/s0960-894x(02)00327-x

  日期：2002.8

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.