HCl*Gly-Gly-Phe-OMe | 61131-29-1

• 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: HCl*Gly-Gly-Phe-OMe
• 英文别名: N-glycyl>-L-3-phenylalanine methyl ester hydrochloride；H-Gly-Gly-Phe-OMe；H2N-Gly-Gly-Phe-OMe*HCl；methyl glycylglycyl-L-phenylalaninate hydrochloride；Gly-Gly-Phe methyl ester；H-Gly-Gly-L-Phe-OMe*HCl；Gly-Gly-Phe-OMe*HCl；methyl (2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoate;hydrochloride
• CAS: 61131-29-1
• 化学式: C₁₄H₁₉N₃O₄*ClH
• 分子量: 329.783
• InChiKey: YWKXMTNWQAJURD-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  110.52
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  HCl*Gly-Gly-Phe-OMe 在 sodium hydroxide 、 四丁基氢氧化铵 、 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 Boc-Tyr(Bzl)-Gly-Gly-Phe-Leu-OBzl
  参考文献：
  名称：

  使用苯基膦酸酯作为偶联剂合成肽

  摘要：

  通过在双（邻或对硝基苯基）苯基膦酸酯存在下用氨基酸酯处理 N-保护的氨基酸（或肽）的四丁基铵盐，可以有效地合成含有各种功能的肽。上述方法采用（3+2）或（4+1）片段偶联方法成功合成亮氨酸-脑啡肽。

  DOI：

  10.1246/cl.1981.65
• 作为产物：
  描述：

  Boc-Gly-Phe-OMe 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 生成 HCl*Gly-Gly-Phe-OMe
  参考文献：
  名称：

  Studies on the synthesis and anti-Osteoporosis of estrogen-GHRPs linkers

  摘要：

  The linkers of estrogen-GHRPs were prepared by the combination of estradiol, estrone, TyrGlyGlyPheLeuOH, and TyrGlyGlyPheLeuOH. Their anti-osteoporosis effect was evaluated by analyzing the data, for instance the weight of the body, femur, femur ash, the content of calcium and phosphor in the femur, the content of calcium and ALP activity in the serum, obtained from the corresponding bioassay in vivo. The results indicated that the anti-osteoporosis potency for estradiol, estrone, TyrGlyGlyPheLeuOH and TyrGlyGlyPheLeuNH(2) may be totally enhanced each other via the corresponding linkers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00847-8

文献信息

• Oligopeptide der β-Carbolin-3-carbonsäure - Synthese und Affinität zu Benzodiazepinrezeptoren
  作者：Klaus-Peter Lippke、Walter E. Müller、Walter Schunack

  DOI：10.1002/ardp.19873200210

  日期：——

  Es wurden Oligopeptide der β‐Carbolin‐3‐carbonsäure dargestellt und deren Affinität zum Benzodiazepinrezeptor in Mäusehirn‐Membranen bestimmt. Über Struktur‐Affinitätsbeziehungen wird berichtet.

  制备了 β-咔啉-3-羧酸的寡肽，并测定了它们对小鼠脑膜中苯二氮卓受体的亲和力。结构 - 报告亲和关系。
• 2-Benzoyl-2-ethoxycarbonylvinyl-1 and 2-benzoylamino-2-methoxy-carbonylvinyl-1 as<i>N</i>-protecting groups in peptide synthesis. Their application in the synthesis of dehydropeptide derivatives containing<i>N</i>-terminal 3-heteroarylamino-2,3-dehydroalanine
  作者：Jurij Svete、Mateja Aljaž-Rožič、Branko Stanovnik

  DOI：10.1002/jhet.5570340128

  日期：1997.1

  and 2-benzoylamino-2-methoxycarbonylvinyl groups in the peptide synthesis. Reactions of ethyl 2-benzoyl-3-dimethylaminopropenoate (6) with α-amino acids gave N-(2-benzoyl-2-ethoxycarbonylvinyl-1)-α-amino acids 13–19. These were coupled with various amino acid esters to form N-(2-benzoyl-2-ethoxycar-bonylvinyl-1)-protected dipeptide esters 20–31. The removal of 2-benzoyl-2-ethoxycarbonylvinyl-1 group

  2-苯甲酰基-3-二甲基氨基丙酸乙酯（6）和2-苯甲酰基氨基-3-二甲基氨基丙酸甲酯（46）被用作保护2-苯甲酰基-2-乙氧基羰基乙烯基-1和2-苯甲酰基氨基-2的氨基的试剂。肽合成中的-甲氧基羰基乙烯基。2-苯甲酰基-3-二甲基氨基丙酸乙酯（6）与α-氨基酸的反应得到N-（2-苯甲酰基-2-乙氧基羰基乙烯基-1）-α-氨基酸13-19。将它们与各种氨基酸酯偶联，形成N-（2-苯甲酰基-2-乙氧基羰基-乙烯基-1）保护的二肽酯20-31。通过肼一盐酸盐或羟胺盐酸盐去除2-苯甲酰基-2-乙氧基羰基乙烯基-1基团，可以高收率得到二肽酯32-41的氢氯化物。类似地，用甘氨酸取代2-苯甲酰基氨基-3-二甲基氨基丙酸甲酯（46）中的二甲基氨基得到N-（2-苯甲酰基氨基-2-甲氧基碳原子-乙烯基-1）甘氨酸（47），其与甘氨酸乙酯偶联得到N- [ N-（2-苯甲酰基氨基-2-甲氧基羰基乙烯基-1）甘氨酰]甘氨酸乙酯（48）。用2-氨基-4
• Carbohydrate Protease Conjugates: Stabilized Proteases for Peptide Synthesis
  作者：Charles A. Wartchow、Peng Wang、Mark D. Bednarski、Matthew R. Callstrom

  DOI：10.1021/jo00112a049

  日期：1995.4

  The synthesis of oligopeptides using stable carbohydrate protease conjugates (CPCs) was examined in acetonitrile solvent systems. CPC[alpha-chymotrypsin] was used for the preparation of peptides containing histidine, phenylalanine, tyrosine, and tryptophan in the P-1 position in 60-93% yield. The CPC[alpha-chymotrypsin]-catalyzed synthesis of octamer Z-Gly-Gly-Phe-Gly-Gly-Phe-Gly-Gly-OEt from Z-Gly-Gly-Phe-Gly-Gly-Phe-OMe was achieved in 71% yield demonstrating that synthesis was the dominant kinetic process relative to amide hydrolysis. CPC[papain] was used to synthesize peptides containing both hydrophilic and hydrophobic amino acids. The Pt specificity of papain for aromatic residues was utilized for the 2 + 3 coupling of Z-Tyr-Gly-OMe to H2N-Gly-Phe-Leu-OH to generate the leucine enkephalin derivative in 79% yield. Although papain is nonspecific for the hydrolysis of N-benzyloxycarbonyl amino acid methyl esters in aqueous solution, the rates of synthesis for these derivitives with nucleophile leucine tert-butyl ester differed by nearly 2 orders of magnitude. CPC[thermolysin] was used to prepare the aspartame precursor Z-Asp-Phe-OMe in 90% yield. The increased stability of CPCs prepared from periodate-modified poly(2-methacrylamido-2-deoxy-D-glucose), poly(2-methacrylamido-2-deoxy-D-galactcose) and poly(5-methacrylamido-5-deoxy-D-ribose), carbohydrate materials designed to increase the aldehyde concentration in aqueous solution, suggests that the stability of CPCs is directly related to the aldehyde concentration of the carbohydrate material. Periodate oxidation of poly(2-methacrylamido-2-deoxy-D-glucose) followed by covalent attachment to a-chymotrypsin gave a CPC with catalytic activity in potassium phosphate buffer at 90 degrees C for 2 h.
• Berger, Edith; Neubert, Klaus; Jakubke, Hans-Dieter, Zeitschrift fur Chemie, 1981, vol. 21, # 1, p. 37
  作者：Berger, Edith、Neubert, Klaus、Jakubke, Hans-Dieter、Kovacs, G. L.

  DOI：——

  日期：——
• Novel thiazolidinedione-5-acetic-acid-peptide hybrid derivatives as potent antidiabetic and cardioprotective agents
  作者：D. Maji、S. Samanta

  DOI：10.1016/j.biopha.2017.01.160

  日期：2017.4

  Thiazolidinediones (TZDs) are one of the important clinically established antidiabetic agents. Aminoacid and peptides have an advantage of better target selectivity and specificity. As hybrids, they also improved absorption and showed better bioavailability, which in turn makes them safer. Hence, here an effort has been made to synthesize hybrids of thiazolidinedione with amino-acids and peptides and evaluate their antidiabetic and cardioprotective effect in streptozotocin-nicotinamide (STZ-NA) induced Type 2 diabetes mellitus (T2DM) rat models.A series of 14 thiazolidinedione-5-acetic acid hybrids with of different amino-acids and peptide combinations were synthesized, characterized and further screened for antidiabetic and cardioprotective activity.Among all, six compounds T1 (SSDMA1), T4 (SSDMA4), T5 (SSDMA5), T7 (SDMA13), T9 (SSDMA15) and T13 (SSDMA49) showed better antioxidant activity and comparable % glucose uptake by yeast cells.Hence, the in vivo antidiabetic screening was done for these six compounds. Among all six T1, T7, T13 showed significant blood glucose level decrease compared to standard pioglitazone HCl. Also T1, T7 and T13 showed better antioxidant activity with lower IC50 value than standard ascorbic acid, and hence in vivo cardioprotective studies were done for these. The ECG studies showed that T1 (SSDMA1) and T7 (SSDMA13) were better effective than SDMA49 (T13) in restoring the normal functioning of the heart, thus may help in preventing the development of diabetic cardiomyopathy (DCM) and controlling T2DM. (C) C 2017 Elsevier Masson SAS. All rights reserved.