Boc-Thr(Bzl)-Pro-OH | 40162-53-6

• 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: Boc-Thr(Bzl)-Pro-OH
• 英文别名: (2S)-1-[(2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoyl]pyrrolidine-2-carboxylic acid
• CAS: 40162-53-6
• 化学式: C₂₁H₃₀N₂O₆
• 分子量: 406.479
• InChiKey: TVWVWRVBFRDUEQ-PVAVHDDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Thr(Bzl)-Pro-OH 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 Boc-Thr(OBn)-Pro-NHMe
  参考文献：
  名称：

  Conformational Changes Associated with Post-Translational Modifications of Pro¹⁴³ in Skp1 of Dictyostelium—A Dipeptide Model System

  摘要：

  Prolyl hydroxylation and subsequent glycosylation of the E3(SCF) ubiquitin ligase subunit Skp1 affects its conformation and its interaction with F-box proteins and, ultimately, O-2-sensing in the organism. Taking a reductionist approach to understand the molecular basis for these effects, a series of end-capped Thr-Pro dipeptides was synthesized, tracking the sequential post-translational modifications that occur in the protein. The conformation of the pyrrolidine ring in each compound was gauged via coupling constants ((3)J(H alpha,H beta)) and the electronegativity of the C gamma-substituents by chemical shifts (C-13). The equilibrium between the cis-trans conformations about the central prolyl peptide bond was investigated by integration of signals corresponding to the two species in the H-1 NMR spectra over a range of temperatures. These studies revealed an increasing preference for the trans-conformation in the order Pro < Hyp < [alpha-(1,4)GlcNAc]Hyp. Rates for the forward and reverse reactions, determined by magnetization transfer experiments, demonstrated a reduced rate for the trans-to-cis conversion and a significant increase in the cis-to-trans conversion upon hydroxylation of the proline residue in the dipeptide. NOE experiments suggest that the Thr side chain pushes the sugar away from the pyrrolidine ring. These effects, which depended on the presence of the N-terminal Thr residue, offer a mechanism to explain altered properties of the corresponding full-length proteins.

  DOI：

  10.1021/ja5033277
• 作为产物：
  描述：

  N-Boc-O-苄基-L-苏氨酸 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Thr(Bzl)-Pro-OH
  参考文献：
  名称：

  Conformational Changes Associated with Post-Translational Modifications of Pro¹⁴³ in Skp1 of Dictyostelium—A Dipeptide Model System

  摘要：

  Prolyl hydroxylation and subsequent glycosylation of the E3(SCF) ubiquitin ligase subunit Skp1 affects its conformation and its interaction with F-box proteins and, ultimately, O-2-sensing in the organism. Taking a reductionist approach to understand the molecular basis for these effects, a series of end-capped Thr-Pro dipeptides was synthesized, tracking the sequential post-translational modifications that occur in the protein. The conformation of the pyrrolidine ring in each compound was gauged via coupling constants ((3)J(H alpha,H beta)) and the electronegativity of the C gamma-substituents by chemical shifts (C-13). The equilibrium between the cis-trans conformations about the central prolyl peptide bond was investigated by integration of signals corresponding to the two species in the H-1 NMR spectra over a range of temperatures. These studies revealed an increasing preference for the trans-conformation in the order Pro < Hyp < [alpha-(1,4)GlcNAc]Hyp. Rates for the forward and reverse reactions, determined by magnetization transfer experiments, demonstrated a reduced rate for the trans-to-cis conversion and a significant increase in the cis-to-trans conversion upon hydroxylation of the proline residue in the dipeptide. NOE experiments suggest that the Thr side chain pushes the sugar away from the pyrrolidine ring. These effects, which depended on the presence of the N-terminal Thr residue, offer a mechanism to explain altered properties of the corresponding full-length proteins.

  DOI：

  10.1021/ja5033277

文献信息

• C-Terminal fragment of human chorionic gonadotropin
  申请人：Toyo Jozo Kabushiki Kaisha

  公开号：US04400316A1

  公开（公告）日：1983-08-23

  A peptide of the formula R-SER-LEU-PRO-SER-PRO-SER-ARG-LEU-PRO-GLY-PRO-SER-ASP-THR-PRO-ILE-LEU-PRO-G LN-OH wherein R: H or R.sub.1 -Ser-Ser-Ser-Ser-Lys-Ala-Pro-Pro-Pro group, R.sub.1 : H or R.sub.2 -R.sub.3 -Asp-Asp-Pro-Arg-Phe-Gln-Asp group, R.sub.2 : H or R.sub.4 -Asp-His-Pro-Leu-Thr group, R.sub.4 : H-R.sub.5 -Gly-Gly-Pro-Lys group, R.sub.5 : Cys or Tyr group, and R.sub.3 : Cys or S-acetamidemethyl-Cys group, or salt thereof, has utility for the preparation of antibodies for assaying human chorionic gonadotropin or as a labelling reagent.

  一种肽的化学式为R-SER-LEU-PRO-SER-PRO-SER-ARG-LEU-PRO-GLY-PRO-SER-ASP-THR-PRO-ILE-LEU-PRO-GLN-OH，其中R：H或R.sub.1-SEr-SEr-SEr-SEr-Lys-Ala-Pro-Pro-Pro基团，R.sub.1：H或R.sub.2-R.sub.3-ASP-ASP-Pro-Arg-Phe-Gln-ASP基团，R.sub.2：H或R.sub.4-ASP-His-Pro-Leu-Thr基团，R.sub.4：H-R.sub.5-Gly-Gly-Pro-Lys基团，R.sub.5：Cys或Tyr基团，R.sub.3：Cys或S-acetamidemethyl-Cys基团，或其盐，可用于制备检测人绒毛膜促性腺激素的抗体或作为标记试剂。
• Polypeptide derivatives and calcium metabolism improving agent
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05204326A1

  公开（公告）日：1993-04-20

  Novel polypeptide derivatives, acid-addition salts thereof and complexes thereof, having the activities for inhibiting bone calcium absorption, for lowering the blood level of calcium, as analgesics, for inhibiting secretion of the gastric juice. Pharmaceutical composition can be prepared by formulating, at least one of the novel polypeptide derivatives, acid-addition salts thereof and complexes thereof, together with a proteolytic enzyme inhibitors and/or pharmaceutically acceptable acids. The pharmaceutical composition are quite effective as agents for curing hypercalcemia, for curing Peget's disease, for curing osteoporosis, analgetic agent, anti-ulcerative agent and the like.

  新型多肽衍生物及其酸加成盐和配合物，具有抑制骨钙吸收、降低血钙水平、作为镇痛剂和抑制胃酸分泌的活性。可以通过将至少一种新型多肽衍生物、其酸加成盐和配合物与蛋白酶抑制剂和/或药用酸一起制剂而成制备药物组合物。该药物组合物对治疗高钙血症、治疗佩吉特病、治疗骨质疏松症、镇痛剂、抗溃疡剂等方面具有相当有效的作用。
• Synthesis of human .beta.-endorphin
  申请人：Hoffmann-La Roche Inc.

  公开号：US04105652A1

  公开（公告）日：1978-08-08

  Human .beta.-endorphin (.beta..sub.h -endorphin) is prepared by solution phase peptide synthesis. Synthesis proceeded via the protected .beta.-endorphin fragments 1-9, 10-18, 19-21 and 22-31.

  人类β-内啡肽（β-endorphin）是通过溶液相肽合成制备的。合成通过保护的β-内啡肽片段1-9、10-18、19-21和22-31进行。
• Synthesis and properties of myelopeptides possessing differentiating activity
  作者：L. A. Fonina、E. V. Kudryavtseva、Zh. D. Bespalova、M. A. Efremov、A. A. Mikhailova、E. A. Kirilina

  DOI：10.1134/s1068162010040035

  日期：2010.7

  Bone marrow peptides Phe-Arg-Pro-Arg-Ile-Met-Thr-Pro (MP-4) and Val-Asp-Pro-Pro (MP-6) have been synthesized by the classical and solid-phase methods of peptide chemistry, and their differentiating activity has been studied on leukemia cell lines HL-60 and K-562. It has been shown that both peptides induce the terminal differentiation of leukemic blasts; however, their mechanisms of action are different.