N-Benzoyl-L-serin-amid | 16707-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Benzoyl-L-serin-amid
• 英文别名: N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]benzamide
• CAS: 16707-67-8
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: UKEZHILAEHRKFA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Benzoyl-L-serin-amid 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 1.5h， 以91%的产率得到Bz-NH-CO-CONH2
  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
• 作为产物：
  描述：

  N-benzoyl-L-serine methyl ester 在 氨 作用下， 以 甲醇 为溶剂， 以75%的产率得到N-Benzoyl-L-serin-amid
  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

• [EN] LUMINESCENT METAL COMPLEXES FOR MONITORING RENAL FUNCTION<br/>[FR] COMPLEXES MÉTALLIQUES LUMINESCENTS POUR LA SURVEILLANCE DES FONCTIONS RÉNALES
  申请人：MALLINCKRODT INC

  公开号：WO2006026038A1

  公开（公告）日：2006-03-09

  Some embodiments of the present invention may be said to be directed to metal complexes of Formula I, wherein at least one of X1, X2, X3, R1, R2, R3, R4 and R5 is what may be characterized as an antenna capable of providing (e.g., absorbing and/or emitting) an appropriate electromagnetic signal. Some embodiments of the present invention are directed to ligands corresponding to metal complexes of Formula I. Some embodiments of the invention are directed to methods of determining renal function using at least one metal complex of Formula I.

  本发明的某些实施例可被称为公式I的金属配合物，其中X1、X2、X3、R1、R2、R3、R4和R5中至少一个可被表征为天线，能够提供（例如吸收和/或发射）适当的电磁信号。本发明的某些实施例涉及与公式I的金属配合物相对应的配体。本发明的某些实施例涉及使用至少一个公式I的金属配合物来确定肾功能的方法。
• Timoshchuk, V. A.; Olimpieva, T. I.; Garbuz, N. I., Journal of general chemistry of the USSR, 1988, vol. 58, # 5, p. 1014 - 1018
  作者：Timoshchuk, V. A.、Olimpieva, T. I.、Garbuz, N. I.

  DOI：——

  日期：——
• TIMOSHCHUK, V. A.;OLIMPIEVA, T. I.;GARBUZ, N. I., ZH. OBSHCH. XIMII, 58,(1988) N 5, 1139-1144
  作者：TIMOSHCHUK, V. A.、OLIMPIEVA, T. I.、GARBUZ, N. I.

  DOI：——

  日期：——
• LUMINESCENT METAL COMPLEXES FOR MONITORING RENAL FUNCTION
  申请人：MALLINCKRODT, INC.

  公开号：EP1793866A1

  公开（公告）日：2007-06-13
• Luminescent Metal Complexes for Monitoring Renal Function
  申请人：Rajagopalan Raghavan

  公开号：US20080299038A1

  公开（公告）日：2008-12-04

  Some embodiments of the present invention may be said to be directed to metal complexes of Formula I, wherein at least one of X 1 , X 2 , X 3 , R 1 , R 2 , R 3 , R 4 and R 5 is what may be characterized as an antenna capable of providing (e.g., absorbing and/or emitting) an appropriate electromagnetic signal. Some embodiments of the present invention are directed to ligands corresponding to metal complexes of Formula I. Some embodiments of the invention are directed to methods of determining renal function using at least one metal complex of Formula I.