FMOC-(S)-2-(二甲基)-3-甲基丁酸 | 203854-59-5

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-(S)-2-(二甲基)-3-甲基丁酸
• 中文别名: (S)-Fmoc-2-氨乙基-3-甲基丁酸盐酸盐
• 英文名称: Fmoc-(S)-β²hVal-OH
• 英文别名: (2S)-2-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-3-methylbutanoic acid；(S)-Fmoc-β²homovaline；(2S)-[{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl]-3-methylbutanoic acid；N-Fmoc-β2-homovaline；(S)-2-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)-3-methylbutanoic acid；(2S)-2-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-3-methylbutanoic acid
• CAS: 203854-59-5
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: WVHQNPPGMKCPTP-GOSISDBHSA-N

物化性质

• 熔点：
  121-123 °C
• 沸点：
  563.9±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  、 FMOC-(S)-2-(二甲基)-3-甲基丁酸 在 N-甲基吗啉 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-7-(2-Chloro-benzyloxycarbonylamino)-3-{(S)-2-[(9H-fluoren-9-ylmethoxycarbonylamino)-methyl]-3-methyl-butyrylamino}-heptanoic acid benzyl ester
  参考文献：
  名称：

  β-肽二级结构通过 Zn2+ 络合强化和强化——在通往β-肽锌指的道路上？

  摘要：

  The correlation between beta(2)-, beta(3)-, and beta(2,3)-amino acid-residue configuration and stability of helix and hairpin-turn secondary structures of peptides consisting of homologated proteinogenic amino acids is analyzed (Figs. 1-3). To test the power of Zn2+ ions in fortifying and/or enforcing secondary structures of beta-peptides, a beta-decapeptide, 1, four beta-octapeptides, 2-5, and a P-hexadecapeptide, 10, have been devised and synthesized. The design was such that the peptides would a) fold to a 14-helix (I and 3) or a hairpin turn (2 and 4), or form neither of these two secondary structures (i.e., 5), and b) carry the side chains of cysteine and histidine in positions, which will allow Zn2+ ions to use their extraordinary affinity for RS- and the imidazole N-atoms for stabilizing or destabilizing the intrinsic secondary structures of the peptides. Tlie beta-hexadecapeptide 10 was designed to a) fold to a turn, to which a 14-helical structure is attached through a P-dipeptide spacer, and b) contain two cysteine and two histidine side chains for Zn complexation, in order to possibly mimic a Zn-finger motif While CD spectra (Figs6-8 and 17) and ESI mass spectra (Figs. 9 and 18) are compatible with the expected effects of Zn 21 ions in all cases, it was shown by detailed NMR analyses of three of the peptides, i.e., 2, 3,5, in the absence and presence of ZnCl2, that i) beta-peptide 2 forms a hairpin turn in H2O, even without Zn complexation to the terminal beta(3)hHis and 3 hCys side chains (Fig. 11), ii) beta-peptide 3, which is present as a 14-helix in MeOH, is forced to a hairpin-turn structure by Zn complexation in H2O (Fig. 12), and iii) beta-peptide 5 is poorly ordered in CD3OH (Fig. 13) and in H2O (Fig. 14), with far-remote beta(3)hCys and beta(3)hHis residues, and has a distorted turn structure in the presence of Zn 21 ions in H2O, with proximate terminal Cys and His side chains.

  DOI：

  10.1002/hlca.339
• 作为产物：
  描述：

  (S)-β-isopripyl-γ-(S)-N-benzyl-α-methylbenzylamino-propylalcohol 在 Jones reagent 、 palladium on carbon 、 甲酸铵 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 FMOC-(S)-2-(二甲基)-3-甲基丁酸
  参考文献：
  名称：

  Hairpin Folding Behavior of Mixed α/β-Peptides in Aqueous Solution

  摘要：

  The invention of new strategies for the design of protein-mimetic oligomers that manifest the folding encoded in natural amino acid sequences is a significant challenge. In contrast to the a-helix, mimicry of protein beta-sheets is less understood. We report here the aqueous folding behavior of a prototype alpha-peptide hairpin model sequence varied at cross-strand positions by incorporation of 16 different beta-amino acid monomers. Our results provide a folding propensity scale for beta-residues in a protein beta-sheet context as well as high-resolution structures of several mixed-backbone alpha/beta-peptide hairpins in water.

  DOI：

  10.1021/ja2002346

文献信息

• Enantioselective synthesis of beta-amino acids using hexahydrobenzoxazolidinones as chiral auxiliaries
  作者：Gloria Reyes-Rangel、Erika Jiménez-González、José Luis Olivares-Romero、Eusebio Juaristi

  DOI：10.1016/j.tetasy.2008.12.023

  日期：2008.12

  A practical synthetic route for the asymmetric synthesis of β2-amino acids is described. In the first step, the procedure involves the N-acylation of readily available, enantiopure hexahydrobenzoxazolidinone (4R,5R)-1 with 3-methylbutanoyl chloride 2, 4-methylpentanoic acid 3, and 3-(1-tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid 4 to afford derivatives 5a, 5b, and 5c, respectively, which were

  对于β的不对称合成的实用合成路线2种α-氨基酸进行说明。在第一步骤中，所述程序包括容易得到的，对映体纯hexahydrobenzoxazolidinone（4的N-酰化- [R，5 - [R ）- 1用3-甲基丁酰氯2，4-甲基戊酸3，和3-（1-叔丁氧羰基） -1 H-吲哚-3-基）丙酸4得到衍生物5a，5b和5c分别通过它们的烯醇钠和溴乙酸苄酯之间的反应以高非对映选择性将其烷基化。的手性从烷基化产物辅助去除，随后氢化和水解，得到β 2 α-氨基酸（小号） - 10A，（小号） - 10B，和（小号） - 10C，这是Ñ -保护用Fmoc。对映异构体（R）-10a – c同样由异构体六氢苯并恶唑烷酮（4 S，5 S）-1制备。; 因此，路线呈现这里提供了访问的有价值的对映体富集的高度β两种对映体2 α-氨基酸。
• Efficient Synthesis of Enantiomerically Pure β²-Amino Acids via Chiral Isoxazolidinones
  作者：Hee-Seung Lee、Jin-Seong Park、Byeong Moon Kim、Samuel H. Gellman

  DOI：10.1021/jo026738b

  日期：2003.2.1

  We report a practical and scalable synthetic route for the preparation of alpha-substituted beta-amino acids (beta(2)-amino acids). Michael addition of a chiral hydroxylamine, derived from alpha-methylbenzylamine, to an alpha-alkylacrylate followed by cyclization gives a diastereomeric mixture of alpha-substituted isoxazolidinones. These diastereomers are separable by column chromatography. Subsequent

  我们报告了一种实用且可扩展的合成路线，用于制备α-取代的β-氨基酸（β（2）-氨基酸）。将衍生自α-甲基苄基胺的手性羟胺迈克尔加成至α-烷基丙烯酸酯，然后环化，得到α-取代的异恶唑烷酮的非对映异构体混合物。这些非对映异构体可通过柱色谱法分离。纯化的异恶唑烷酮的随后氢化，然后进行Fmoc保护，得​​到对映体纯的Fmoc-β（2）-氨基酸，可用于合成β-肽。该途径提供了获得保护的β（2）-氨基酸的两种对映异构体的途径。
• Preparation ofN-Fmoc-Protected ?2- and ?3-Amino Acids and their use as building blocks for the solid-phase synthesis of ?-peptides
  作者：Gilles Guichard、Stefan Abele、Dieter Seebach

  DOI：10.1002/hlca.19980810202

  日期：1998.2.4

  solid-phase synthesis apparatus using conventional solid-phase peptide synthesis procedures (Scheme 3). In the case of β3-peptides, two methods were used to anchor the first β-amino acid: esterification of the ortho-chlorotrityl chloride resin with the first Fmoc-β-amino acid 2 (Method I, Scheme 2) or acylation of the 4-(benzyloxy)benzyl alcohol resin (Wang resin) with the ketene intermediates from the Wolff

  受N -Fmoc保护的（Fmoc =（9 H-氟-9-基甲氧基）羰基）β-氨基酸是在固相支持物上高效合成β-寡肽所必需的。对映体纯的Fmoc-β 3 -氨基酸β 3：侧链和NH 2在C（3）（= C（β））从Fmoc保护的（制备小号） -和（- [R）-α-氨基酸与脂族，芳香族和官能化侧链，使用标准或优化的Arndt-Eistert反应顺序。将Fmoc-β 2 -氨基酸（β 2在C（2），NH侧链2（中C 3）（= C（β）））配置轴承丙氨酸，缬氨酸，亮氨酸，和Phe的侧链合成经由所述埃文斯'手性助剂的方法。目标β 3个-heptapeptides 5-8，一个β 3 -十五肽9和β 2 -heptapeptide 10使用常规的固相肽合成方法（在手动固相合成装置合成方案3）。在β的情况下3 -肽，两种方法被用于锚定所述第一β氨基酸：酯化的邻-chlorotrityl氯乙烯树脂与所述第一的
• Synthesis and Biological Evaluation of Gramicidin S-Inspired Cyclic Mixed<i>α</i>/<i>β</i>-Peptides
  作者：Matthijs van der Knaap、Fatih Basalan、Henny C. van de Mei、Henk J. Busscher、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1002/cbdv.201200277

  日期：2012.11

  β(2)-amino acids (R)- and (S)-Fmoc-β(2)homovaline and (R)-Fmoc-β(2)homoleucine are synthesized. These building blocks were used, in combination with commercially available α- and β(3)-amino acids, for the synthesis of the cyclo-(αβ(3)αβ(2)α)(2) peptide 2 and the cyclo-(αβ(2)αβ(3)α)(2) peptides 3-5. The peptides 2-5 were screened for their ability to inhibit a small panel of Gram-negative and Gram-positive bacterial

  通过涉及二苄基亚胺类物质和埃文斯手性酰化恶唑烷酮的钛烯酸酯的曼尼希反应，β（2）-氨基酸（R）-和（S）-Fmoc-β（2）同卵磷脂和（R）-Fmoc-β （2）合成了高亮氨酸。这些构件与可商购的α-和β（3）-氨基酸结合使用，用于合成环-（αβ（3）αβ（2）α）（2）肽2和​​环-（ αβ（2）αβ（3）α）（2）肽3-5。筛选肽2-5抑制一小批革兰氏阴性和革兰氏阳性细菌菌株的能力。
• Design, synthesis and structural analysis of mixed α/β-peptides that adopt stable cyclic hairpin-like conformations
  作者：Matthijs van der Knaap、José M. Otero、Antonio Llamas-Saiz、Mark J. van Raaij、Lianne I. Lageveen、Henk J. Busscher、Gijsbert M. Grotenbreg、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1016/j.tet.2012.01.015

  日期：2012.3

  replacement of four α-amino acid residues of a cyclo-(ααααα)2 peptide by β-, β2- or β3-amino acids residues provided a series of novel 2:1 α/β-mixed peptides that were designed to adopt cyclic hairpin-like structures. It was shown that conformationally stable cyclo-(αβαβα)2 isomers can be obtained using both enantiomers of the central two basic α-amino acid residues, a known α-amino acid turn sequence and several

  战略更换四个α氨基的一个氨基酸残基的环- （ααααα）2肽通过β-，β 2 -和β 3 -氨基酸残基而提供一系列新2:1α/β混合的肽设计，即采用环状发夹状结构。结果表明，构象稳定的环-（αβαβα）2异构体可以使用中心两个碱性α-氨基酸残基的两个对映异构体，已知的α-氨基酸转向序列以及没有侧链或具有特定区域和区域的疏水性侧链的面对的β-氨基酸残基的几种组合来获得。立体化学。两种衍生物的X射线分析提供了分子内氢键相互作用，主链二面角和新型环状发夹状结构的侧链位置的分子细节。这些异构体之一在晶体结构中形成了前所未有的六边形纳米通道组件。