N-(叔丁氧羰基)-L-丙氨酸(氮15) | 139952-87-7

• 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
• 中文名称: N-(叔丁氧羰基)-L-丙氨酸(氮15)
• 中文别名: BOC-丙氨酸-15N；N-(叔-丁氧基羰基)-L-丙氨酸-15N
• 英文名称: Boc-¹⁵N-Ala
• 英文别名: Boc-[15N]ala-OH；(2S)-2-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino]propanoic acid
• CAS: 139952-87-7
• 化学式: C₈H₁₅NO₄
• 分子量: 190.205
• InChiKey: QVHJQCGUWFKTSE-LBBOFACRSA-N

物化性质

• 熔点：
  79-83 °C (lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

制备方法与用途

用途：用于15N标记多肽的合成。

反应信息

• 作为反应物：
  描述：

  N-(叔丁氧羰基)-L-丙氨酸(氮15) 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 44.5h， 生成 Boc-¹⁵N-Ala-Gly
  参考文献：
  名称：

  用于超灵敏蛋白质组定量的同位素稳定同位素 N-磷酸化标记 (iSIPL)

  摘要：

  一种新型的同量异位磷试剂能够以高灵敏度进行准确的定量蛋白质组分析和肽测序。具有特征 P−N 键的报告离子簇以非常高的强度有效地生成，用于蛋白质定量。

  DOI：

  10.1002/anie.202303656
• 作为产物：
  描述：

  benzyl (S)-N-(t-butoxycarbonyl)<15N>alaninate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以786 mg的产率得到N-(叔丁氧羰基)-L-丙氨酸(氮15)
  参考文献：
  名称：

  Degerbeck, Fredrik; Fransson, Bengt; Grehn, Leif, Journal of the Chemical Society. Perkin transactions I, 1992, # 2, p. 245 - 254

  摘要：

  DOI：

文献信息

• Stereochemical Requirements for β-Hairpin Formation:  Model Studies with Four-Residue Peptides and Depsipeptides
  作者：Tasir S. Haque、Jennifer C. Little、Samuel H. Gellman

  DOI：10.1021/ja960429j

  日期：1996.1.1

  associated with β-hairpins containing a two-residue loop between the strand segments. Each of our four-residue molecules contains proline at the second position, to promote a central β-turn. The β-turn is induced to be either “common” or “mirror-image”, relative to the outer residues, by choice of residue configuration (l vs d). In methylene chloride, end-capped tetrapeptide Ac−l-Val-d-Pro-d-Ala-l-Leu-NMe2

  提供了一系列可以形成最小 β-发夹（两个分子内氢键）的四肽和类似缩肽的光谱和晶体学数据。这些模型化合物已被用于检验“镜像”β-转角促进 β-发夹形成的假设。这一假设的灵感来自对球状蛋白中 β-发夹的统计调查 (Sibanda, BL; Thornton, JM Nature 1985, 316, 170)，该调查显示镜像 β-转角（I' 型和 II' 型），尽管通常很少见，通常与在链段之间包含两个残基环的 β-发夹相关。我们的四个残基分子中的每一个都在第二个位置含有脯氨酸，以促进中心 β-转角。相对于外部残基，β-转角被诱导为“普通”或“镜像”，通过选择残基配置（l vs d）。在二氯甲烷中，封端的四肽 Ac-l-Val-d-Pro-d-Ala-l-Leu-NMe2 主要折叠成 β-发夹构象，而 d...
• Determination of the mutual orientation of the 15N and 13C NMR chemical shift tensors of 13-15N double labeled model peptides for silk fibroin from the dipolar-coupled powder patterns
  作者：Tetsuo Asakura、Yasunobu Yamazaki、Koo Wey Seng、Makoto Demura

  DOI：10.1016/s0022-2860(98)00291-9

  日期：1998.5

  C]Gly[ 15 N]AlaGlyAla-OPac and Boc-[1- 13 C]Gly[ 15 N]ValGlyAla-OPac, where Boc is t-butoxycarbonyl, OMe is methyl ester, OPac is phenacyl ester, Ala is alanine, Gly is glycine and Val is valine. From the comparisons of the 15 N chemical shift tensors and the orientations of the principal axis system relative to the molecular symmetry axes among three compounds having [1- 13 C]Ala[ 15 N]Gly units, it

  摘要 确定了家蚕丝的 13 C 15 N 双标记模型肽的 15 N 和 13 C 羰基碳位点的 15 N 和 13 C 化学位移张量，以及主轴系统相对于分子对称轴的取向。丝心蛋白，即 Boc-[1- 13 C]Ala[ 15 N]Gly-OMe、Boc-[1- 13 C]Ala[ 15 N]GlyAlaGly-OPac、Boc-AlaGly[1- 13 C]Ala[ 15 N]GlyAlaGly-OPac、Boc-[1- 13 C]Gly[ 15 N]AlaGlyAla-OPac、Boc-GlyAla[1- 13 C]Gly[ 15 N]AlaGlyAla-OPac 和 Boc-[1- 13 C] Gly[ 15 N]ValGlyAla-OPac，其中 Boc 是叔丁氧基羰基，OMe 是甲酯，OPac 是苯甲酰酯，Ala 是丙氨酸，Gly 是甘氨酸，Val 是缬氨酸。从具有 [1- 13
• Regulating Antifreeze Activity through Water: Latent Functions of the Sugars of Antifreeze Glycoprotein Revealed by Total Chemical Synthesis
  作者：Ryo Okamoto、Ryo Orii、Hiroyuki Shibata、Yuta Maki、Sakae Tsuda、Yasuhiro Kajihara

  DOI：10.1002/chem.202203553

  日期：——

  The total chemical synthesis of antifreeze glycoprotein (AFGP) derivatives including partially sugar deleted forms and unnatural forms incorporating glucose-type sugars instead of galactose-type sugars of the natural form is described. These elaborated AFGPs indicate a unique function of the sugar residues that form a unique dynamic water phase, thereby inhibiting freezing.

  描述了抗冻糖蛋白 (AFGP) 衍生物的全化学合成，包括部分糖缺失形式和包含葡萄糖型糖而不是天然形式的半乳糖型糖的非天然形式。这些精心制作的 AFGP 表明糖残基具有独特的功能，可形成独特的动态水相，从而抑制冻结。
• Reversible Enolization of β-Amino Carboxamides by Lithium Hexamethyldisilazide
  作者：Anne J. McNeil、David B. Collum

  DOI：10.1021/ja043470s

  日期：2005.4.1

  The enolization of beta-amino carboxamides by lithium hexamethyldisilazide (LiHMDS) in THF/ toluene and subsequent diastereoselective alkylation with CH3I are reported. In situ IR spectroscopic studies reveal that P-amino carboxamides coordinate to LiHMDS at -78 degrees C before enolization. Comparison with structurally similar carboxamides suggests that the P-amino group promotes the enolization. I R spectroscopic studies also show that the enolization is reversible. Efficient trapping of the enolate by CH3I affords full conversion to products. Li-6 and N-15 NMR spectroscopic studies reveal that lithium enolate-LiHMDS mixed dimers and trimers as well as a homoaggregated enolate are formed during the reaction. At ambient temperature, racemization of the beta-position through a putative reversible Michael addition was observed.
• ISOBARIC STABLE ISOTOPE-CONTAINING PHOSPHORYLATED PROTEIN LABELING REAGENT, AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：GUANGDONG PHOBIOLOGY TECH CO., LTD

  公开号：US20230150897A1

  公开（公告）日：2023-05-18

  An isobaric stable isotope-containing phosphorylated protein labeling reagent, and a preparation method and application thereof are provided. The protein labeling reagent is a phosphorylated dipeptide organophosphorus reagent labeled by a stable isotope such as deuterium-2, carbon-13, oxygen-18, or nitrogen-15. The preparation method includes: (1) preparation of an isobaric stable isotope-containing amino acid with N-terminal protection, (2) preparation of an isobaric stable isotope-containing amino acid activated ester Fmoc/Boc-R 1 -NHS with N-terminal protection, (3) preparation of an isobaric stable isotope-containing dipeptide, (4) preparation of an isobaric stable isotope-containing phosphite, (5) preparation of an isobaric stable isotope-containing phosphite dipeptide, and (6) preparation of a stable isotope-labeled N-phosphorylated amino acid activated ester. The present protein labeling reagent can realize the quantitative analysis of polypeptides, standard proteins, proteins in cells, and proteins in urine samples and blood samples, and has the advantages of good accuracy, high sensitivity, no interference of isotope effect and wide applicability.