O-benzyl-D-tyrosine benzyl ester | 134950-91-7

• 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: O-benzyl-D-tyrosine benzyl ester
• 英文别名: (R)-Benzyl 2-amino-3-(4-(benzyloxy)phenyl)propanoate；benzyl (2R)-2-amino-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 134950-91-7
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: UCRXQUVKDMVBBM-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-benzyl-D-tyrosine benzyl ester 、 N-benzyloxycarbonyl-L-isoleucyl-O-benzyl-L-tyrosine 在 2,4,6-三甲基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79.3%的产率得到N-benzyloxycarbonyl-L-isoleucyl-O-benzyl-L-tyrosyl-O-benzyl-D-tyrosine benzyl ester
  参考文献：
  名称：

  Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26

  摘要：

  The naturally occurring phosphonotripeptide K-26 is a potent angiotensin converting enzyme (ACE) inhibitor containing an alpha-amino phosphonic acid analogue of tyrosine. Previous studies have demonstrated that canonical peptide analogues of K-26 are micromolar inhibitors of ACE. To ascertain the structure-activity relationships in this class of ACE inhibitory natural products, K-26 and eight analogues were chemically synthesized and evaluated. Phosphonyl substitution was found to be the critical determinant of activity, resulting in a 1500-fold increase in ACE inhibition versus carboxyl analogues. Secondarily, the absolute configuration of the terminal alpha-amino phosphonate and N-acetylation were found to significantly modulate ACE inhibitory activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.130
• 作为产物：
  描述：

  benzyl 3-[4-(benzyloxy)phenyl]-(2R)-2-{[(tert-butoxy)carbonyl]amino}propanoate 在 三氟乙酸 作用下， 以 苯甲醚 为溶剂， 反应 0.5h， 以50.4%的产率得到O-benzyl-D-tyrosine benzyl ester
  参考文献：
  名称：

  Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26

  摘要：

  The naturally occurring phosphonotripeptide K-26 is a potent angiotensin converting enzyme (ACE) inhibitor containing an alpha-amino phosphonic acid analogue of tyrosine. Previous studies have demonstrated that canonical peptide analogues of K-26 are micromolar inhibitors of ACE. To ascertain the structure-activity relationships in this class of ACE inhibitory natural products, K-26 and eight analogues were chemically synthesized and evaluated. Phosphonyl substitution was found to be the critical determinant of activity, resulting in a 1500-fold increase in ACE inhibition versus carboxyl analogues. Secondarily, the absolute configuration of the terminal alpha-amino phosphonate and N-acetylation were found to significantly modulate ACE inhibitory activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.130

文献信息

• Pharmacologically active peptide derivatives and pharmaceutical
  申请人：SPA Societa' Prodotti Antibiotici S.p.A.

  公开号：US05182265A1

  公开（公告）日：1993-01-26

  Peptide derivatives and their salts with pharmaceutically acceptable acids or bases, having the general formula (I), ##STR1## wherein R=--H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 acyl, alkoxycarbonyl with C.sub.1 -C.sub.4 alkyl; R.sub.1 =--H, C.sub.1 -C.sub.3 alkyl; R.sub.2 =--H, --OH, --OR'.sub.2, wherein R'.sub.2 =C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 acyl, benzyl; R.sub.3 =--H, --CH.sub.3 ; n=1,2 R.sub.4 =--H, --COOH, --CONH.sub.2, --COOR'.sub.4, wherein R'.sub.4 =C.sub.1 -C.sub.3 alkyl, benzyl; R.sub.5 =--H, 4--OH, 3,4--OH, --OR'.sub.5 wherein R'.sub.5 =C.sub.1 -3 alkyl, C.sub.1 -C.sub.3 acyl, benzyl; R.sub.6 =--OH, --NH.sub.2, --OR'.sub.6 wherein R'.sub.6 =C.sub.1 -C.sub.3 alkyl, benzyl; endowed with analgesic, antiviral, immuno-modulating pharmacological properties, and the pharmaceutical forms containing them as active ingredients.

  肽衍生物及其与药学上可接受的酸或碱盐，具有一般式(I)，其中R= -H，C1-C3烷基，C1-C3酰基，C1-C4烷基的烷氧羰基; R1 = -H，C1-C3烷基; R2 = -H，-OH，-OR'2，其中R'2 = C1-C3烷基，C1-C3酰基，苄基; R3 = -H，-CH3; n = 1,2 R4 = -H，-COOH，-CONH2，-COOR'4，其中R'4 = C1-C3烷基，苄基; R5 = -H，4-OH，3,4-OH，-OR'5，其中R'5 = C1-C3烷基，C1-C3酰基，苄基; R6 = -OH，-NH2，-OR'6，其中R'6 = C1-C3烷基，苄基; 具有镇痛、抗病毒、免疫调节药理学性质，并且含有它们作为活性成分的药物制剂。
• Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26
  作者：Ioanna Ntai、Brian O. Bachmann

  DOI：10.1016/j.bmcl.2007.11.130

  日期：2008.5

  The naturally occurring phosphonotripeptide K-26 is a potent angiotensin converting enzyme (ACE) inhibitor containing an alpha-amino phosphonic acid analogue of tyrosine. Previous studies have demonstrated that canonical peptide analogues of K-26 are micromolar inhibitors of ACE. To ascertain the structure-activity relationships in this class of ACE inhibitory natural products, K-26 and eight analogues were chemically synthesized and evaluated. Phosphonyl substitution was found to be the critical determinant of activity, resulting in a 1500-fold increase in ACE inhibition versus carboxyl analogues. Secondarily, the absolute configuration of the terminal alpha-amino phosphonate and N-acetylation were found to significantly modulate ACE inhibitory activity. (c) 2007 Elsevier Ltd. All rights reserved.