Boc-D-天冬酰胺 | 200192-48-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: Boc-D-天冬酰胺
• 中文别名: N-叔丁氧羰基-N'-氧蒽基-D-天门冬酰胺；N-叔丁氧羰基-N-氧蒽基-D-天门冬氨酸
• 英文名称: Boc-D-Asn(Xan)-OH
• 英文别名: (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-(9H-xanthen-9-ylamino)butanoic acid
• CAS: 200192-48-9
• 化学式: C₂₂H₂₄N₂O₆
• mdl: MFCD00076910
• 分子量: 412.442
• InChiKey: YMGDQLXBNMRJMR-OAHLLOKOSA-N

物化性质

• 沸点：
  650.7±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.318
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-D-天冬酰胺 生成 C₁₇H₂₈N₃O₅PolS
  参考文献：
  名称：

  Mirror Image Forms of Snow Flea Antifreeze Protein Prepared by Total Chemical Synthesis Have Identical Antifreeze Activities

  摘要：

  The recently discovered glycine-rich snow flea antifreeze protein (sfAFP) has no sequence homology with any known proteins. No experimental structure has been reported for this interesting protein molecule. Here we report the total chemical synthesis of the mirror image forms of sfAFP (i.e., L-sfAFP, the native protein, and D-sfAFP, the native protein's enantiomer). The predicted 81 amino acid residue polypeptide chain of sfAFP contains Cys residues at positions 1, 13, 28, and 43 and was prepared from four synthetic peptide segments by sequential native chemical ligation. After purification, the full-length synthetic polypeptide was folded at 4 degrees C to form the sfAFP protein containing two disulfides. Chemically synthesized sfAFP had the expected antifreeze activity in an ice recrystallization inhibition assay. Mirror image D-sfAFP protein was prepared by the same synthetic strategy, using peptide segments made from D-amino acids, and had an identical but opposite-sign CD spectrum. As expected, D-sfAFP displays the same antifreeze properties as L-sfAFP, because ice presents an achiral surface for sfAFP binding. Facile synthetic access to sfAFP will enable determination of its molecular structure and systematic elucidation of the molecular basis of the antifreeze properties of this unique protein.

  DOI：

  10.1021/ja801352j
• 作为产物：
  描述：

  生成 Boc-D-天冬酰胺
  参考文献：
  名称：

  Mirror Image Forms of Snow Flea Antifreeze Protein Prepared by Total Chemical Synthesis Have Identical Antifreeze Activities

  摘要：

  The recently discovered glycine-rich snow flea antifreeze protein (sfAFP) has no sequence homology with any known proteins. No experimental structure has been reported for this interesting protein molecule. Here we report the total chemical synthesis of the mirror image forms of sfAFP (i.e., L-sfAFP, the native protein, and D-sfAFP, the native protein's enantiomer). The predicted 81 amino acid residue polypeptide chain of sfAFP contains Cys residues at positions 1, 13, 28, and 43 and was prepared from four synthetic peptide segments by sequential native chemical ligation. After purification, the full-length synthetic polypeptide was folded at 4 degrees C to form the sfAFP protein containing two disulfides. Chemically synthesized sfAFP had the expected antifreeze activity in an ice recrystallization inhibition assay. Mirror image D-sfAFP protein was prepared by the same synthetic strategy, using peptide segments made from D-amino acids, and had an identical but opposite-sign CD spectrum. As expected, D-sfAFP displays the same antifreeze properties as L-sfAFP, because ice presents an achiral surface for sfAFP binding. Facile synthetic access to sfAFP will enable determination of its molecular structure and systematic elucidation of the molecular basis of the antifreeze properties of this unique protein.

  DOI：

  10.1021/ja801352j

文献信息

• Total chemical synthesis and X-ray structure of kaliotoxin by racemic protein crystallography
  作者：Brad L. Pentelute、Kalyaneswar Mandal、Zachary P. Gates、Michael R. Sawaya、Todd O. Yeates、Stephen B. H. Kent

  DOI：10.1039/c0cc03148h

  日期：——

  Here we report the total synthesis of kaliotoxin by 'one pot' native chemical ligation of three synthetic peptides. A racemic mixture of D- and L-kaliotoxin synthetic protein molecules gave crystals in the centrosymmetric space group P1 that diffracted to atomic-resolution (0.95 A), enabling the X-ray structure of kaliotoxin to be determined by direct methods.

  在这里，我们报告了通过三种合成肽的“一锅”天然化学连接进行的kaliotoxin的总合成。D-和L-钾毒素合成蛋白分子的外消旋混合物在中心对称空间群P1中产生晶体，衍射至原子分辨率（0.95 A），从而可以通过直接方法确定钾毒素的X射线结构。
• X-ray Structure of Native Scorpion Toxin BmBKTx1 by Racemic Protein Crystallography Using Direct Methods
  作者：Kalyaneswar Mandal、Brad L. Pentelute、Valentina Tereshko、Anthony A. Kossiakoff、Stephen B. H. Kent

  DOI：10.1021/ja8077973

  日期：2009.2.4

  Racemic protein crystallography, enabled by total chemical synthesis, has allowed us to determine the X-ray structure of native scorpion toxin BmBKTx1; direct methods were used for phase determination. This is the first example of a protein racemate that crystallized in space group I41/a.

  外消旋蛋白质晶体学，通过全化学合成，使我们能够确定天然蝎子毒素 BmBKTx1 的 X 射线结构；直接法用于相位测定。这是在空间群 I41/a 中结晶的蛋白质外消旋体的第一个例子。
• Total chemical synthesis of human proinsulin
  作者：Samuel Luisier、Michal Avital-Shmilovici、Michael A. Weiss、Stephen B. H. Kent

  DOI：10.1039/c0cc03141k

  日期：——

  A convergent synthetic strategy based on modern chemical ligation methods was used to make human proinsulin. The synthetic protein was characterized by LCMS, CD spectroscopy, and by 1D- and 2D-NMR spectroscopy. Synthetic human proinsulin had full biochemical activity in a receptor-binding assay.

  基于现代化学连接方法的合成策略被用于制造人前胰岛素。通过液相色谱质谱（LCMS）、圆二色光谱学（CD）以及一维和二维核磁共振（NMR）光谱学对合成蛋白质进行了表征。合成的人前胰岛素在受体结合试验中显示出完全的生物化学活性。
• Radiation Damage and Racemic Protein Crystallography Reveal the Unique Structure of the GASA/Snakin Protein Superfamily
  作者：Ho Yeung、Christopher J. Squire、Yuliana Yosaatmadja、Santosh Panjikar、Gemma López、Antonio Molina、Edward N. Baker、Paul W. R. Harris、Margaret A. Brimble

  DOI：10.1002/anie.201602719

  日期：2016.7.4

  radiation‐damage‐induced phasing (RIP), is reported. Racemic crystals of snakin‐1 and quasi‐racemic crystals incorporating an unnatural 4‐iodophenylalanine residue were prepared from chemically synthesized d‐ and l‐proteins. Breakage of the C−I bonds in the quasi‐racemic crystals facilitated structure determination by RIP. The crystal structure reveals a unique protein fold with six disulfide crosslinks, presenting

  GASA / snakin超家族的蛋白质在植物蛋白质组中很常见，并且具有多种功能，包括激素串扰，发育和防御。该家族的一个63个残基成员snakin-1是一种来自马铃薯的抗菌蛋白，以前已经以化学合成的形式形成了完全活性的形式。本文报道了snakin-1的1.5Å结构，该结构由外消旋蛋白质结晶和辐射损伤诱导的定相（RIP）的新颖组合确定。snakin-1的外消旋晶体和掺有非天然4-碘苯基丙氨酸残基的准外消旋晶体是由化学合成的d和l制备的蛋白。准外消旋晶体中CI键的断裂促进了RIP的结构确定。晶体结构揭示了具有六个二硫键交联的独特蛋白质折叠，呈现出可将蛋白质靶向微生物细胞表面的独特静电表面。