Boc-Lys(Z)-Gly-OH | 53613-24-4

• 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-Lys(Z)-Gly-OH
• 英文别名: N-α-tert-butyloxycarbonyl-N-ε-benzyloxycarbonyl-lysyl-glycine；N-(N^α-tert-butoxycarbonyl-N^ε-carbobenzoxy-L-lysyl)glycine；2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]amino]acetic acid
• CAS: 53613-24-4
• 化学式: C₂₁H₃₁N₃O₇
• 分子量: 437.493
• InChiKey: DRMHFQTWTBJDAF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  143.06
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Boc-Lys(Z)-Gly-OH 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 (tert-butoxycarbonyl)-L-lysylglycine
  参考文献：
  名称：

  Design of high-affinity peptide conjugates with optimized fluorescence quantum yield as markers for small peptide transporter PEPT1 (SLC15A1)

  摘要：

  We employed a computational approach to design and synthesize a series of. fluorescently labeled hPEPT1 substrates. Five Alexa Fluor-350 (TM)-labeled peptides were assessed for their in vitro inhibitory activity in hPEPT1-transfected CHO cells. At least four labeled peptides show potent inhibitory activity toward hPEPT1-mediated uptake of [H-3]-GlySar and three compounds displayed a significant cellular uptake specifically mediated by hPEPT1. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.044
• 作为产物：
  描述：

  N-(N^α-tert-butoxycarbonyl-N^ε-carbobenzoxy-L-lysyl)glycine ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 生成 Boc-Lys(Z)-Gly-OH
  参考文献：
  名称：

  Saito; Matsui; Fukushima, Arzneimittel-Forschung/Drug Research, 1989, vol. 39, # 12, p. 1558 - 1561

  摘要：

  DOI：

文献信息

• Amino acids and peptides. IX Synthesis and physicochemical properties of cyclic peptides.
  作者：KAZUTAKA TANIZAWA、KUNIO OKUMURA、HIROMI ITOH、YASUMARU HATANAKA、YUICHI KANAOKA

  DOI：10.1248/cpb.34.4001

  日期：——

  A series of cyclic peptides varying in ring size and in amino acid constituents was synthesized. Cyclization reactions of linear peptides were carried out by the azide, p-nitrophenyl ester, N-hydroxysuccinimide ester and diethyl phosphorocyanidate methods. Intermolecular cyclodimerization was also applied for the preparation of a cyclic hexapeptide. The reaction yield in each cyclization method was found to be sufficient for preparative purposes. Conformational analysis of the cyclic peptides was carried out by using proton nuclear magnetic resonance. The temperature dependency of peptide NH signals revealed that hexapeptides with the cyclo(-Gly-Xxx-Gly-)2 sequence are stabilized by intramolecular hydrogen bonding and are resistant to temperatureinduced conformational change.

  合成了一系列环状肽，具有不同的环大小和氨基酸成分。通过叠氮化物、对硝基苯基酯、N-羟基琥珀酰亚胺酯和二乙基磷氰酸盐法对线性肽进行环化反应。还应用了分子间环二聚化法制备环状六肽。每种环化方法的反应产率均被发现足够用于制备目的。使用质子核磁共振对环状肽进行了构象分析。肽NH信号的温度依赖性表明，具有环状(-Gly-Xxx-Gly-)2序列的六肽通过分子内氢键得到稳定，并且对温度诱导的构象变化具有抗性。
• Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides
  作者：Subhendu Sekhar Bag、Suranjan De

  DOI：10.1016/j.bmcl.2018.02.021

  日期：2018.5

  The solvatochromic IR responsivity of small side chain-NCS in two unexplored unnatural amino acids, isothiocyanyl alanine ((NCS)Ala = Ita) and lysine ((NCS)Lys = Itl), without perturbing the conformation is demonstrated in two designed short tripeptide (BocAla-(NCS)Ala-Ala-OMe) and hexapeptide (BocLeu-ValPhe- Phe-(NCS)Lys-Gly-OMe). Demonstration of site specific fluorescent labeling in both the peptides and ligation type reaction in (NCS)Lys indicates the novelty of these two amino acids as alternative to the available canonical amino acids. (C) 2018 Published by Elsevier Ltd.
• Synthesis of N-Urethane Protected α-Aminoalkyl-α′-cyanomethyl Ketones; Application to the Synthesis of 3-Substituted 5-Amino-1H-pyrazole Tethered Peptidomimetics
  作者：Vommina Sureshbabu、M. Sharnabai、G. Nagendra

  DOI：10.1055/s-0032-1316586

  日期：2012.8

  The preparation of N-protected amino/peptide alpha-cyanomethyl ketones through cyanation of the corresponding alpha-bromomethyl ketones is described. The utility of the resulting acyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the alpha-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected D-and L-Ala-OH as model substrates. The synthesis of peptide pyrazolecarbox-amides is also delineated.
• Immunoactive peptides. IV. Ercagnine — An immunoactive fragment of histone H2A
  作者：V. P. Ivanova、E. I. Sorochinskaya

  DOI：10.1007/bf00770613

  日期：1992.9
• SHIBNEV, V. A.;SHARETSKIJ, A. N.;VALIEV, R. V.;XALIKOV, SH. X., BIOORGAN. XIMIYA, 16,(1990) N, S. 926-932
  作者：SHIBNEV, V. A.、SHARETSKIJ, A. N.、VALIEV, R. V.、XALIKOV, SH. X.

  DOI：——

  日期：——