N-Alpha-苯甲酰基-L-苯丙氨酸酰胺 | 72150-35-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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-Alpha-苯甲酰基-L-苯丙氨酸酰胺
• 中文别名: N-Α-苯甲酰基-L-苯丙氨酸酰胺
• 英文名称: Bz-Phe-NH2
• 英文别名: N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]benzamide
• CAS: 72150-35-7
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: GDJKEUNPXYLPHG-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Alpha-苯甲酰基-L-苯丙氨酸酰胺 、 丙炔酸乙酯 在 sodium acetate 、 palladium diacetate 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 0.08h， 以31%的产率得到ethyl (S,Z)-3-(2-benzamido-3-phenylpropanamido)acrylate
  参考文献：
  名称：

  铜催化β-硼β-氨基酯的对映选择性合成

  摘要：

  在该报告中，公开了β-酰胺基丙烯酸酯的对映选择性的铜催化的硼酸酯化。已经使用廉价的铜催化剂和可商购的手性配体制备了具有一致高水平对映体控制的多种生物学上重要的生物学重要的α-氨基硼酸酯。该方法可用于合成新型的含硼二肽和半硼酸酯。

  DOI：

  10.1021/acs.orglett.7b02784
• 作为产物：
  描述：

  Bz-Phe-Ser-OMe 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 1.5h， 以79%的产率得到N-Alpha-苯甲酰基-L-苯丙氨酸酰胺
  参考文献：
  名称：

  Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission

  摘要：

  alpha-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)catalyzed C-alpha-C side-chain scission. Facets associated with this novel cu-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides-thus acting as Gly equivalents in simulating the alpha-amidating action of pituitary enzymes-those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C-alpha and C side-chain bond), resulting in the generation of alpha-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C-alpha-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [Pep-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX],wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.

  DOI：

  10.1021/ja00094a008

文献信息

• Asymmetric Hydrogenation with Chiral Aminophosphine–Rhodium Complexes and Chiral Recognition by Bisphosphine–Rhodium Complexes in the Asymmetric Hydrogenation of Olefins through the Chiral Helical Conformation of Phenyl Groups on the Phosphorus Atom
  作者：Ken-ichi Onuma、Tomiyasu Ito、Asao Nakamura

  DOI：10.1246/bcsj.53.2016

  日期：1980.7

  rhodium complex of (1R,2R)-1,2-bis(diphenylphosphinamino)cyclohexane by the N-methylation of the ligand in asymmetric hydrogenation has been described. From stereochemical considerations, the chiral helical conformation of the phenyl groups attached on the phosphorus in bisphosphine-rhodium complexes may be responsible for the induced chirality of the product of the hydrogenation. A complex with a left-handed

  据报道，α-酰基氨基肉桂酸与（1R,2R）-1,2-双（N-二苯基膦基-N-甲基氨基）环己烷的铑络合物的不对称氢化反应优先生成（S）-氨基酸。相反，已经发现对映体(R)-氨基酸是通过用(1R,2R)-1,2-双(二苯基膦氨基)环己烷的铑络合物氢化而获得的。已经描述了通过配体的 N-甲基化在不对称氢化中对 (1R,2R)-1,2-双（二苯基膦氨基）环己烷的铑配合物的立体选择性反转的研究。从立体化学的角度来看，双膦-铑配合物中与磷相连的苯基的手性螺旋构象可能是氢化产物诱导手性的原因。具有左旋螺旋的复合物将产生 (R)-氨基酸，具有右旋螺旋的复合物将产生 (S)-氨基酸。溶剂和基材结构的影响...
• Identification of 1,5,7-Triazabicyclododecene and Polystyrene-Supported Superbases as Efficient Hydroxylaminolysis Agents of Sterically Hindered and Epimerizable Esters
  作者：Loic Tomas、Craig Harris、Romain Pierre、Frédéric Gaigne、Ghizlane El-Bazbouz、Grégoire Mouis、Gilles Ouvry

  DOI：10.1055/s-0036-1591551

  日期：2018.5

  discovery programs. In this letter, we communicate the identification of 1,5,7-triazabicyclododecene and polystyrene-supported superbases as efficient hydroxylaminolysis agents of sterically hindered and epimerizable esters and, to some extent, amides, using iChem Explorer® as the conditions scouting tool.

  在现代药物研究中，需要以受控方式制备化学库的可靠方案对于推动药物发现计划中的设计-制造-测试循环至关重要。在这封信中，我们使用 iChem Explorer® 作为条件探索工具，将 1,5,7-三氮杂双环十二烯和聚苯乙烯支持的超强碱鉴定为位阻和差向异构酯的有效羟氨解剂，在某种程度上，酰胺。
• [EN] PRODUCTS AND METHODS FOR THE TREATMENT OF MIXTURES OF WATER AND HYDROPHOBIC LIQUIDS<br/>[FR] PRODUITS ET PROCÉDÉS POUR LE TRAITEMENT DE MÉLANGES D'EAU ET DE LIQUIDES HYDROPHOBES
  申请人：B C RES INC

  公开号：WO2019232629A1

  公开（公告）日：2019-12-12

  Chemical-based methods and products for mitigating the impact of an oil spill are disclosed. The products act by herding, thickening, gelling, and reducing adhesiveness. N-fatty acid amino acid (FA-AA) conjugates display oil-herding behavior when formulated as a free acid in water-miscible organic solvents. A water-miscible organic solvent is not required if the FA-AA conjugate is formulated as a salt. Various salts of FA-AA conjugates are water soluble and can herd oils and increase the thickness of the oil layer. Replacement of the acid group of fatty acid α-amino acid conjugates with other groups that act as hydrogen bond donors and acceptors results in potent phase selective organo-gellants. The oil spill herders can be prepared from bio-based feedstocks and are biodegradable. The oil thickeners or gellants, which are prepared from bio-based feedstocks, have low toxicity, high capacity for oil and reduce the need to use an organic solvent to apply the thickener or gellant to the oil and water mixture in order to gel the oil phase. Formulae (IB), (II), (III)

  本发明涉及化学方法和产品，用于减轻油污泄漏的影响。这些产品通过聚集、增稠、胶化和降低粘性来发挥作用。当N-脂肪酸氨基酸（FA-AA）共轭物被制成水溶性有机溶剂中的自由酸时，它们具有聚集油的行为。如果FA-AA共轭物被制成盐，则不需要水溶性有机溶剂。各种FA-AA共轭物的盐是水溶性的，可以聚集油并增加油层的厚度。将脂肪酸α-氨基酸共轭物的酸基替换为其他作为氢键供体和受体的基团，可以得到有效的相选择性有机胶凝剂。这些油污聚集剂可以从生物基原料制备，并且是可生物降解的。从生物基原料制备的油稠剂或胶凝剂具有低毒性，对油具有高容量，并且减少了使用有机溶剂将稠剂或胶凝剂应用于油水混合物以胶化油相的需要。公式（IB）、（II）、（III）。
• Novel diphenylmethyl-Derived Amide Protecting Group for Efficient Liquid-Phase Peptide Synthesis: AJIPHASE
  作者：Daisuke Takahashi、Tatsuya Yano、Tatsuya Fukui

  DOI：10.1021/ol302002g

  日期：2012.9.7

  An efficient method for the synthesis of peptides bearing an amide at the C-terminal is described. This method involves the attachment of a C-terminal protecting group bearing long aliphatic chains, followed by the repetition of simple reaction and precipitation steps with the combined advantages of liquid-phase peptide synthesis (LPPS) and solid-phase peptide synthesis (SPPS). Using this method, a hydrophobic peptide was successfully synthesized in good yield and high purity, which cannot be obtained satisfactorily by SPPS.
• Brutsche, Andreas; Hartke, Klaus, Liebigs Annalen der Chemie, 1992, # 9, p. 921 - 926
  作者：Brutsche, Andreas、Hartke, Klaus

  DOI：——

  日期：——