N-BOC-S-4-甲基苄基-D-半胱氨酸 | 61925-78-8

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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-BOC-S-4-甲基苄基-D-半胱氨酸
• 中文别名: N-(叔丁氧羰基)-S-(4-甲基苄基)-D-半胱氨酸
• 英文名称: (S)-2-(tert-butoxycarbonyl)amino-3-(4-methylbenzylthio)propanoic acid
• 英文别名: Boc-D-Cys(4-CH3Bzl)-OH；N-Boc-D-Cys(4-MeBzl)；Boc-^DCys(MeBzl)-OH；(2S)-3-[(4-methylphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 61925-78-8
• 化学式: C₁₆H₂₃NO₄S
• 分子量: 325.429
• InChiKey: CUNVVZWSABRKAL-CYBMUJFWSA-N

物化性质

• 沸点：
  493.8±45.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-BOC-S-4-甲基苄基-D-半胱氨酸 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以480 mg的产率得到(S)-2-(tert-butoxycarbonyl)amino-3-(4-methylbenzylsulfonyl)propanoic acid
  参考文献：
  名称：

  Combination of Non-natural d-Amino Acid Derivatives and Allophenylnorstatine−Dimethylthioproline Scaffold in HIV Protease Inhibitors Have High Efficacy in Mutant HIV

  摘要：

  Several non-natural D-amino acid derivatives were introduced as P(2)/P(3) residues in allophenylnorstatine-containing (Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid) HIV protease inhibitors. The synthetic analogues exhibited potent inhibitory activity against HIV-1 protease enzyme and HIV-1 replication in MT-4 cells. Structure-activity relationships revealed that D-cysteine or serine derivatives contributed to highly potent anti-HIV activities. Interestingly, anti-HIV activity of all the D-amino acid-introduced inhibitors was remarkably enhanced in their anti-HIV activities against a Nelfinavir-resistant clone, which has a D30N mutation in the protease, over that of the wild-type strain. HIV inhibitory activity of several analogues was moderately affected by an inclusion of alpha(1)-acid glycoprotein in the test medium.

  DOI：

  10.1021/jm701555p
• 作为产物：
  描述：

  4-甲基苄基硫醇 、 N-叔丁氧羰基-D-丝氨酸(Β-内酯) 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.34h， 以88%的产率得到N-BOC-S-4-甲基苄基-D-半胱氨酸
  参考文献：
  名称：

  Combination of Non-natural d-Amino Acid Derivatives and Allophenylnorstatine−Dimethylthioproline Scaffold in HIV Protease Inhibitors Have High Efficacy in Mutant HIV

  摘要：

  Several non-natural D-amino acid derivatives were introduced as P(2)/P(3) residues in allophenylnorstatine-containing (Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid) HIV protease inhibitors. The synthetic analogues exhibited potent inhibitory activity against HIV-1 protease enzyme and HIV-1 replication in MT-4 cells. Structure-activity relationships revealed that D-cysteine or serine derivatives contributed to highly potent anti-HIV activities. Interestingly, anti-HIV activity of all the D-amino acid-introduced inhibitors was remarkably enhanced in their anti-HIV activities against a Nelfinavir-resistant clone, which has a D30N mutation in the protease, over that of the wild-type strain. HIV inhibitory activity of several analogues was moderately affected by an inclusion of alpha(1)-acid glycoprotein in the test medium.

  DOI：

  10.1021/jm701555p

文献信息

• Synthesis and biological property of .ALPHA.-human atrial natriuretic peptide analogs with a constrained or stereochemically modified cyclic moiety.
  作者：Yoshiharu MINAMITAKE、Mayumi FURUYA、Yasuo KITAJIMA、Maki TAKEHISA、Shoji TANAKA

  DOI：10.1248/cpb.38.1920

  日期：——

  Conformationally restricted analogs of α-human atrial natriuretic peptide (α-hANP) containing L- or D-penicillamine, or D-cysteine in place of cysteine residues at positions 7 and 23 were synthesized by the liquid phase procedure. Their biological properties in the assays of receptor binding and cyclic guanosine monophosphate (cGMP) accumulation employing rat vascular smooth muscle cells (VSMC), vasorelaxant activity using rat isolated aorta were evaluated. We found that the constrained and/or stereochemically altered ring moiety generally did not influence the receptor binding activity, however, cGMP accumulation and vasorelaxant activities were quite sensitive to conformational perturbation. Furthermore, a lack of correlation between cGMP acccumulation activity and vasorelaxant activity was observed. Dissociation between these activities was typical in the case of [DPen7, 23]-α-hANP(7-28), which showed quite weak vasorelaxant activity in spite of its full cGMP accumulation and receptor binding potencies. This result suggests that cGMP accumulation alone is not sufficient to promote AMP-induced vasorelaxation, and that the other second messenger (s) may mediate this activity.

  通过液相法合成了α-人心房钠尿肽（α-hANP）的构象限制性类似物，这些类似物在第7和23位氨基酸残基上分别含有L型或D型的青霉胺，或D型的半胱氨酸。我们评估了这些化合物的生物学特性，包括利用大鼠血管平滑肌细胞（VSMC）进行的受体结合试验和环磷酸鸟苷（cGMP）积累试验，以及使用大鼠离体主动脉进行的血管舒张活性试验。我们发现，受限制和/或立体化学改变的环结构通常不影响受体结合活性，然而，环磷酸鸟苷积累和血管舒张活性对构象扰动相当敏感。此外，我们观察到环磷酸鸟苷积累活性与血管舒张活性之间缺乏相关性。在这些活性之间表现出典型分离的是[DPen7, 23]-α-hANP(7-28)，尽管它具有完全的环磷酸鸟苷积累和受体结合效力，但其血管舒张活性相当弱。这一结果表明，仅环磷酸鸟苷的积累不足以促进ANP诱导的血管舒张，其他第二信使可能介导这一活性。
• 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。
• 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。
• Substitution on the Phe3 aromatic ring in cyclic .delta. opioid receptor-selective dermorphin/deltorphin tetrapeptide analogs: electronic and lipophilic requirements for receptor affinity
  作者：Deborah L. Heyl、Henry I. Mosberg

  DOI：10.1021/jm00087a006

  日期：1992.5

  receptor recognition in a series of conformationally restricted tetrapeptides related to the cyclic, delta opioid receptor-selective analogue, [formula: see text] electronic, lipophilic, and steric effects at the Phe3 residue were assessed by substitution at different positions of the side-chain aromatic ring by halogens, alkyl, hydroxyl, and nitro groups. Effects on opioid receptor binding affinity

  为了探索影响与环状，δ阿片受体选择性类似物有关的一系列构象受限的四肽中影响受体识别的结构特征，通过取代评估了对Phe3残基的电子，亲脂和空间效应在侧链芳环的不同位置上的卤素，烷基，羟基和硝基。确定了对阿片样物质受体结合亲和力和选择性的影响。该结果通常与线性和环状五肽脑啡肽的类似修饰的报道一致，表明空间，亲脂性和电子性质都是δ阿片受体识别的重要决定因素。特别，增加亲脂性或对芳环施加吸电子作用的修饰增强结合亲和力，而亲水，庞大或释放电子的修饰是有害的。这些观察结果与线性阿片类五肽脑啡肽类似物中Phe4修饰的定量构效关系（QSAR）结果非常吻合，表明Phe3四肽侧链和Phe4五肽侧链与相同的δ受体结合亚位相互作用。