α-D-galactopyranosyl azide | 106192-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-galactopyranosyl azide
• 英文别名: alpha-d-Galactopyranosyl azide；(2S,3R,4S,5R,6R)-2-azido-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 106192-39-6
• 化学式: C₆H₁₁N₃O₅
• 分子量: 205.17
• InChiKey: KSRDTSABQYNYMP-PHYPRBDBSA-N

物化性质

• 熔点：
  75-77 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  α-D-galactopyranosyl azide 在 lithium bromide 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 24.0h， 生成 2,3,4-Tri-O-acetyl-6-brom-6-desoxy-α-D-galactopyranosylazid
  参考文献：
  名称：

  Gyoergydeak, Zoltan; Szilagyi, Laszlo, Liebigs Annalen der Chemie, 1987, p. 235 - 242

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 六甲基磷酰三胺 、 aluminum (III) chloride 、 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 α-D-galactopyranosyl azide
  参考文献：
  名称：

  β-半乳糖苷酶催化亲核试剂的诱变保留残留水解活性并提供转半乳糖苷酶

  摘要：

  突变能力：来自环状芽孢杆菌(BgaD-A)的 β-半乳糖苷酶活性位点中催化亲核试剂 E532 的定点诱变表明，构建没有水解活性的突变体（糖合酶）的常用方法并非适用于所有保留糖苷酶。BgaD-A 突变体保留了残留的水解活性并充当转半乳糖苷酶。

  DOI：

  10.1002/cctc.202101107

文献信息

• ¹⁸F-Glyco-RGD Peptides for PET Imaging of Integrin Expression: Efficient Radiosynthesis by Click Chemistry and Modulation of Biodistribution by Glycosylation
  作者：Simone Maschauer、Roland Haubner、Torsten Kuwert、Olaf Prante

  DOI：10.1021/mp4004817

  日期：2014.2.3

  small-animal PET imaging using U87MG tumor-bearing nude mice. [18F]6Glc-RGD and [18F]Mlt-RGD showed significantly decreased liver and kidney uptake by PET relative to the 2-[18F]fluoroglucosyl analog [18F]2Glc-RGD, and showed specific tumor uptake in vivo. Notably, [18F]Mlt-RGD revealed uptake and retention in the U87MG tumor comparable to that of [18F]Galacto-RGD. Both [18F]6Glc-RGD and [18F]Mlt-RGD were

  糖基化经常改善大分子在体内的生物动力学和清除特性，因此可用于设计正电子发射断层扫描（PET）的放射性药物。最近，我们已经开发了一种用于靶向整联蛋白受体的带有炔烃的RGD肽的18 F-氟糖基化的点击化学方法。为了研究该策略是否可以产生具有良好生物动力学的18 F标记RGD糖肽，我们生成了一系列新的RGD糖肽，将6-氟糖基残基从单糖转变为二糖单元，从而提供了糖基（[ 19 F] 6Glc- RGD，4b），半乳糖基（[ 19 F] Gal-RGD，4c），麦芽糖基（[ 19 F] Mlt-RGD，4e）和纤维二糖基（[ 19 F] Cel-RGD，4f）结合的肽，产率高，纯度> 97％。所有这些RGD糖肽表现出高亲和力α v β 3（11-55纳米），α v β 5（6-14纳米），以及α v β 3个阳性U87MG细胞（90-395纳米）。18 F-使用隐秘辅助反应条件（CH 3 CN，85
• A Spontaneous Single-Crystal-to-Single-Crystal Polymorphic Transition Involving Major Packing Changes
  作者：Baiju P. Krishnan、Kana M. Sureshan

  DOI：10.1021/ja512697g

  日期：2015.2.4

  4,6-O-Benzylidene-alpha-d-galactosyl azide crystallizes into two morphologically distinct polymorphs depending on the solvent. While the a form appeared as thick rods and crystallized in P2(1) space group (monoclinic) with a single molecule in the asymmetric unit, the beta form appeared as thin fibers and crystallized in P1 space group (triclinic) with six molecules in the asymmetric unit. Both the polymorphs appeared to melt at the same temperature. Differential scanning calorimetry analysis revealed that polymorph alpha irreversibly undergoes endothermic transition to polymorph beta much before its melting point, which accounts for their apparently same melting points. Variable temperature powder X-ray diffraction (PXRD) experiments provided additional proof for the polymorphic transition. Single-crystal XRD analyses revealed that alpha to beta transition occurs in a single-crystal-to-single-crystal (SCSC) fashion not only under thermal activation but also spontaneously at room temperature. The SCSC nature of this transition is surprising in light of the large structural differences between these polymorphs. Polarized light microscopy experiments not only proved the SCSC nature of the transition but also suggested nucleation and growth mechanism for the transition.
• Design, synthesis and immunological evaluation of 1,2,3-triazole-tethered carbohydrate–Pam 3 Cys conjugates as TLR2 agonists
  作者：Naresh Nalla、Preethi Pallavi、Bonam Srinivasa Reddy、Sreekanth Miryala、V. Naveen Kumar、Mohammed Mahboob、M. Sampath Kumar Halmuthur

  DOI：10.1016/j.bmc.2015.06.070

  日期：2015.9

  Novel triazolyl Pam(3)Cys conjugates encompassing various carbohydrate entities have been synthesized by copper mediated azide-alkyne click chemistry protocol with a view to probe the SAR pertaining to their adjuvant activity in conjunction with OVA as antigen. The preliminary ex vivo cytokine profiling revealed optimal Th1 activation and the in vivo adjuvant studies of ribose derived hybrid (6e) revealed a marked improvement in the OVA specific antibody IgG response and Th1 cytokine expressions. The triazolyl Pam(3)Cys carbohydrate conjugates were found to be the hTLR2 agonists as revealed by their SEAP activity due to NFKB activation. The described protocol is the first successful attempt of the amalgamation of carbohydrate-Pam(3)Cys motifs tethered to a triazole linker as a peptide free adjuvant. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthèse directe d'azotures de glycosyle
  作者：Moulay-Larbi Larabi、Catherine Fréchou、Gilles Demailly

  DOI：10.1016/s0040-4039(00)76789-x

  日期：1994.4

  Azidation of some unprotected aldoses with the Ph(3)P-N-chlorosuccinimide-LiN3 system leads regioselectively to glycosyl azides; 1,2-trans compounds are obtained stereoselectively.