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1.
用微波辐射技术,以葡甲胺为催化剂、水为溶剂,于800W功率下回流反应100min,成功对(R)-萘普生进行消 旋,收率为95%.方法操作简单,反应时间短,后处理简便. 相似文献
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We have reported that two aspartyl (Asp-151 and Asp-58) residues in αA-crystallin in human eye lens were inverted to the D-isomer and isomerized to β-aspartyl residues with age. We report here the kinetics of the Asp racemization of three model peptides corresponding to fragments of αA-crystallin: IQTGLD151ATHAER (T18 peptide). TVLD58SGISEVR (T6 peptide) and HFSPED84LTVK (T10 peptide, as a control). The rate constants of the racemization of Asp residues in these peptides were measured at pH 7.0. at five temperatures: 50, 60, 70, 80 and 90 °C. From the Arrhenius equation, we estimated the activation energy (E) of racemization and the time required for the Asp D/L ratio to approximate to 1.0 (D/L ratio of Asp = 0.99) at body temperature. For the peptide T18, E=21.4 kcal/mol and t=13.5 yr. For the peptide T6, E= 26.8 kcal/mol and t= 49.5 yr. For the control peptide T10, E=28.3 kcal/mol and t= 78.1 yr. The racemization rate of Asp in these three peptides is parallel to that of Asp residues in αA-crystallin. The racemization rate of Asp in the T18 peptide was very rapid compared to that in the other peptides. This result also reflects the racemization rate in native αA-crystallin 相似文献
4.
3-Dimethylphosphinothioyl-2(3H)-oxazolone (MPTO) was synthesized, and its ability to effect racemization-free couplings and cyclization of a peptide and its C-terminal epimer was examined. MPTO showed good reactivity in aprotic polar solvents such as N,N-dimethylformamide (DMF) and N-methylpyrrolidone. In reactivity MPTO resembles DPPA and dimethylphosphinothioyl azide (MPTA) previously developed by us, but it is much better than these reagents because the side reactions specific to the azide method could be avoided. In coupling of Z-Gly-Val-OH with H-Val-OMe in DMF at 0°C, no racemization was observed without use of racemization-suppressing additives. Slight racemization observed at room temperature could be completely suppressed by addition of HOBt but not by HOSu. The utility of MPTO was demonstrated by the synthesis of cyclo-(d -Trp-d -Glu(OBzl)-Ala-D-Val-Leu), an intermediate for an endothelin-binding inhibitor BE 18257A. In a comparative study using DPPA, MPTA and MPTO, no racemization was observed for MPTA or MPTO, while DPPA caused considerable racemization. When MPTO was used in the presence of HOBt rapid cyclization (3 h at RT) occurred to give the optically pure cyclic product. 相似文献
5.
NICOLAY V. KULIKOV STEPHAN S. BASOK NICOLAY G. LUKYANENKO 《Chemical biology & drug design》1993,42(1):20-23
A series of model DCC-mediated couplings of Z-Pro-D-Leu-OH with 2,3-benzo-10-aza-1,4,7,13-tetraoxacyclopentadeca-2-ene were studied by high-performance liquid chromatography. It was found that racemization during preparation of N-(Z-Pro-Leu-)benzoaza-15-crown-5 is promoted by HOBT, an additive usually reducing this process. 相似文献
6.
S. Ritz R. Stock H. W. Schütz H. -J. Kaatsch 《International journal of legal medicine》1995,108(3):135-139
Determination of age at death on the basis of aspartic acid racemization in dentin is one of the most reproducible and accurate methods. In Germany, age estimation by this method has so far generally not been applied to living persons, since the extraction of a tooth exclusively for age estimation when it is not medically indicated is regarded as ethically and legally problematic. The development of a biopsy technique applicable to dentin took place against this background. Testing the technique and analysis of dentinal biopsy specimens revealed that the biopsy technique is a low-risk procedure that causes only minor discomfort to the affected person. It is readily practicable and facilitates standardized specimen removal. The relationship between the extent of aspartic acid racemization in dentinal biopsy specimens and age is very close, facilitating age estimation. A prerequisite for accurate results is the performance of biopsies under strictly standardized conditions. If this is guaranteed, age determination on the basis of aspartic acid racemization in dentinal biopsy specimens appears to be superior in precision to most other methods in living persons and can be used for all age groups. 相似文献
7.
蛋白质结构中L-氨基酸可通过外消旋化转化为D-氨基酸,蛋白质中氨基酸的外消旋化可影响蛋白质的空间结构和功能,并证实与一些疾病的发生相关。随着分析仪器技术的不断发展,蛋白质中氨基酸外消旋化分析方法及检测技术也在不断地更新。本文综述了蛋白质中氨基酸外消旋化与疾病的关系、影响外消旋化的因素以及氨基酸外消旋化的检测方法,并对蛋白质中氨基酸外消旋化的研究方向进行了展望。 相似文献
8.
TOSHIFUMI MIYAZAWA TOSHIHIKO OTOMATSU TAKASHI YAMADA SHIGERU KUWATA 《Chemical biology & drug design》1992,39(3):229-236
Separation of protected epimeric peptides, Z-Gly-Xaa-Xbb-OMe (where Xaa and Xbb = chiral amino acid residues), by reversed-phase HPLC was utilized for studying racemization in peptide synthesis. Thus, the following factors which might affect the extent of racemization during the coupling by the carbodiimide method were investigated: the combination of amino acid residues to be coupled, coexisting tertiary amine salts, and the relative configuration of the amino acid residues. The following points were revealed: the combination of bulky residues at the coupling site results in extensive racemization in a polar solvent such as DMF, the amine hydrochlorides cause less racemization than the p-toluenesulfonates in DMF, and the influence of relative configuration differs depending on the solvent and the individuality of the amino components. Furthermore, the racemization-suppressing effect of some additives in the carbodiimide method was reevaluated by employing the same procedure. 相似文献
9.
New 2,3,5,6-tetrafluorophenyl active esters of protected amino acids useful for peptide synthesis were prepared in high yield. For certain amino acid derivatives such as Boc-Pro-OH, Boc-Ile-OH, and Boc-Val-OH, their tetrafluorophenyl esters have significantly higher melting points than the corresponding pentafluorophenyl esters. Kinetic studies were carried out to compare the racemization rate constants (with triethylamine) and coupling rate constants (with valine methyl ester) of the tetrafluorophenyl and pentafluorophenyl esters of protected histidine and tyrosine. Results of the second-order kinetics showed similarly large kcoupling/kracemization ratios for both tetra- and pentafluorophenyl esters. In particular, the use of 2,3,5,6-tetrafluorophenyl or pentafluorophenyl ester prevents extensive racemization of the N-tert.-butyloxycarbonyl-Nim-benzyl-histidine. 相似文献
10.
A method for the isolation and identification of C-terminal peptides of proteins has been developed. The procedure entails the racemization of the C-terminal amino acid by reaction of the N-trifluoroacetylated protein with acetic anhydride and pyridine. After deprotection, the protein is fragmented to yield a mixture of peptides, which in turn are digested with carboxypeptidases. All peptides are hydrolyzed to L-amino acids except the C-terminal peptide with the terminal D-amino-acid residue. It is resistant to the action of carboxypeptidases and is readily identified by peptide mapping. © Munksgaard 1995. 相似文献