Bz-Leu-NH2 | 16709-42-5

• 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: Bz-Leu-NH2
• 英文别名: Benzoylleucinamid；N-[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]benzamide
• CAS: 16709-42-5
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: TUTYDIRXNJGWDX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  Bz-Leu-NH2 、 triethyloxonium fluoroborate 在 硫化氢 作用下， 生成 N-Benzoyl-L-thioleucin-O-ethylester
  参考文献：
  名称：

  Brutsche, Andreas; Hartke, Klaus, Liebigs Annalen der Chemie, 1992, # 9, p. 921 - 926

  摘要：

  DOI：
• 作为产物：
  描述：

  Bz-Leu-Thr-OMe 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 1.5h， 以72%的产率得到Bz-Leu-NH2
  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

• Selective conversion of primary amides to esters promoted by KHSO4
  作者：Narsimha Sattenapally、Jhanvi Sharma、Yuqing Hou

  DOI：10.24820/ark.5550190.p010.392

  日期：——

  Primary amides, either aliphatic or aromatic, are easily converted to the corresponding esters via reflux in lower primary alcohols in the presence of KHSO4. Secondary amides lead to complicated mixtures under analogous conditions, whereas tertiary amides were inert. Use of isopropyl alcohol resulted in the formation of product at slower rate and lower yield along with side products, whereas, use of

  在 KHSO4 存在下，通过在低级伯醇中回流，脂肪族或芳香族伯酰胺很容易转化为相应的酯。仲酰胺在类似条件下会导致复杂的混合物，而叔酰胺是惰性的。异丙醇的使用导致产物的形成速度较慢，产率较低，同时副产物也较低，而使用叔醇不能成功转化，烯丙醇和苯甲醇提供了复杂的混合物。
• NOVEL COMPOUNDS
  申请人：CICHY-KNIGHT Maria

  公开号：US20090124619A1

  公开（公告）日：2009-05-14

  This invention relates to novel compounds useful in the treatment of diseases associated with TRPV4 channel receptor. More specifically, this invention relates to certain substituted morpholines and piperidines, according to Formula I wherein: X is O or CH 2 ; R1 is optionally substituted C 3-7 cycloalkyl, C 3-6 cycloalkyl-C 0-6 alkyl, optionally substituted C 4-7 cycloalkenyl, optionally substituted Het-C 0-7 alkyl, optionally substituted Het-C 0-7 alkenyl, optionally substituted aryl, optionally substituted heterocycloalkyl, or optionally substituted heteroaryl; R2 is H, branched or optionally substituted C 1-6 alkyl, C 3-6 cycloalkyl-C 0-6 alkyl, Ar—C 0-6 alkyl, or Het-C 0-6 alkyl; and R3 is optionally substituted heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl; or pharmaceutically acceptable salts, hydrates, solvates and physiologically functional derivatives thereof.

  本发明涉及一种在治疗与TRPV4通道受体相关的疾病中有用的新化合物。更具体地说，本发明涉及某些取代的吗啡啶和哌啶，其符合式I，其中：X为O或CH2；R1为可选取代的C3-7环烷基、C3-6环烷基-C0-6烷基、可选取代的C4-7环烷烯基、可选取代的Het-C0-7烷基、可选取代的Het-C0-7烯基、可选取代的芳基、可选取代的杂环烷基或可选取代的杂环芳基；R2为H、支链或可选取代的C1-6烷基、C3-6环烷基-C0-6烷基、Ar-C0-6烷基或Het-C0-6烷基；R3为可选取代的杂环烷基、可选取代的芳基或可选取代的杂环芳基；或其药学上可接受的盐、水合物、溶剂化物和生理学上的功能衍生物。
• Bergmann; Zervas; Fruton, Journal of Biological Chemistry, 1936, vol. 115, p. 593,607
  作者：Bergmann、Zervas、Fruton

  DOI：——

  日期：——
• RANGANATHAN, DARSHAN;SAINI, SUJATA, J. AMER. CHEM. SOC., 113,(1991) N, C. 1042-1044
  作者：RANGANATHAN, DARSHAN、SAINI, SUJATA

  DOI：——

  日期：——
• Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission
  作者：Darshan Ranganathan、Narendra K. Vaish、Kavita Shah

  DOI：10.1021/ja00094a008

  日期：1994.7

  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.