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Synthesis of a highly hydrophobic cyclic decapeptide by solid-phase synthesis of linear peptide and cyclization in solution 被引量:5
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作者 Chen, Jian Zhang, Bei +2 位作者 Xie, Cao Lu, Yi Wu, Wei 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第4期391-394,共4页
A general method was described to synthesize a highly hydrophobic cyclic peptide,cyclo[LWLWLWLWLQ]where underlines indicate D-configuration of the amino acid,by a two-step solid-phase/solution synthesis strategy.The l... A general method was described to synthesize a highly hydrophobic cyclic peptide,cyclo[LWLWLWLWLQ]where underlines indicate D-configuration of the amino acid,by a two-step solid-phase/solution synthesis strategy.The linear decapeptide was assembled by standard Boc chemistry on solid-phase and subsequently cyclized in solution with high efficiency and reproducibility. In subsequent purification by semi-preparative HPLC,50%(v/v) DMF/H_2O was employed as the solvent to overcome the difficulty of solubilization... 展开更多
关键词 Cyclic peptide Decapeptide cyclo[LWLWLWLWLQ] solid-phase synthesis CYCLIZATION PURIFICATION
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Solid-Phase Enzymatic Peptide Synthesis to Produce an Antioxidant Dipeptide
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作者 Yuyao Shan Mengfan Wang +2 位作者 Wei Qi Rongxin Su Zhimin He 《Transactions of Tianjin University》 EI CAS 2019年第3期276-282,共7页
Peptide bond synthesis is favorable to the production of bioactive small peptides. However, the abuse of toxic reagents remains an issue for chemical synthesis method, whereas the low product yield and purity limit th... Peptide bond synthesis is favorable to the production of bioactive small peptides. However, the abuse of toxic reagents remains an issue for chemical synthesis method, whereas the low product yield and purity limit the widespread use of enzymatic method. In this study, a new solid-phase enzymatic peptide synthesis(SPEPS) strategy was developed to produce an antioxidant tyrosine-alanine dipeptide(Tyr-Ala) by using recombinant carboxypeptidase Y(CPY) as the catalyst. The general SPEPS procedure involves three steps. First, the N-protected acyl donor was covalently attached to solid resin. Second,the peptide bond was condensed between the acyl donor and the nucleophile under the catalysis of CPY. Finally, one-step cleavage was performed to remove the protecting group and cleave the peptides from solid resin. Upon the optimization of reaction conditions, 77.92%(±2.723%) yield of Tyr-Ala with high product purity of 90.971%(±2.695%) was obtained.In addition, the antioxidant activity of Tyr-Ala was determined by ABTS method, indicating that the synthesized Tyr-Ala obtained by SPEPS showed a superior antioxidant capability compared with commercial glutathione. 展开更多
关键词 solid-phase ENZYMATIC peptide synthesis CARBOXYpeptidASE Y Tyrosine-alanine Antioxidant activity
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Solid Phase Peptide Synthesis of Fusukang for AIDS
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作者 甘一如 戴琦 +1 位作者 张雪竹 高晨昊 《Transactions of Tianjin University》 EI CAS 2003年第4期289-291,共3页
A 36-residue peptide is designed to cure acquired immunodeficiency syndrome(AIDS), and is synthesized by the manual solid phase peptide synthesis technique. Different reaction conditions of the synthesis process were ... A 36-residue peptide is designed to cure acquired immunodeficiency syndrome(AIDS), and is synthesized by the manual solid phase peptide synthesis technique. Different reaction conditions of the synthesis process were discussed. Stirring efficiency of mechanics and nitrogen was compared. The mechanical method displays a predominant performance. Although the coupling efficiencies of diisopropylcarbodiimide(DIC) and dicyclohexylcarbodiimide(DCC) are virtually identical, DIC offers several advantages over DCC in practice due to different physical characters. Wash conditions after deprotection and coupling were investigated to monitor washing efficiency. 0.369 2 g crude peptide was obtained. 展开更多
关键词 solid phase peptide synthesis stirring efficiency coupling reagent wash conditions
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Synthesis of Nitrogen-containing Cyclopeptides from N-Terminal Lysine Precursor on Solid Supports
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作者 XiaoXiaoYANG ChuanLiangQIU DeXinWANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2005年第6期755-758,共4页
Three synthetic routes for the preparation of nitrogen containing cyclic compounds have been developed, in which the assembling of Fomc-Lys(Boc) residue at N-terminal of resin-bound intermediates is a key prerequisite... Three synthetic routes for the preparation of nitrogen containing cyclic compounds have been developed, in which the assembling of Fomc-Lys(Boc) residue at N-terminal of resin-bound intermediates is a key prerequisite. Six peptides with nitrogen containing local cyclic structure were efficiently synthesized in good yield starting from chloromethyl resin. 展开更多
关键词 Local-cyclic peptides intramolecular cyclization solid-phase synthesis pseudo-dilution effect.
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Study on Chemical Synthesis and Insecticidal Activity of Peptideκ-CTx-btg02 被引量:1
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作者 Qin CHEN Jinxing FU +1 位作者 Min XU Bingmiao GAO 《Agricultural Biotechnology》 CAS 2021年第4期59-62,共4页
[Objectives]This study was conducted to investigate the chemical synthesis of peptideκ-CTx-btg02.[Methods]Linear peptideκ-CTx-btg02 was synthesized by solid phase peptide synthesis(SPPS).After oxidation and folding ... [Objectives]This study was conducted to investigate the chemical synthesis of peptideκ-CTx-btg02.[Methods]Linear peptideκ-CTx-btg02 was synthesized by solid phase peptide synthesis(SPPS).After oxidation and folding of the linear peptide,mass spectrometry identification and high performance liquid chromatography(HPLC)purification were performed.Then,the MTT method and insect injection method were applied to study its insecticidal activity.[Results]The peptideκ-CTx-btg02 was successfully synthesized by the SPPS method,and identified for the formation of disulfide bonds by mass spectrometry identification,and the purity after HPLC separation was greater than 95%.The MTT experiment showed that the peptideκ-CTx-btg02 could inhibit the growth of insect cells sf9,with a half effective dose of 0.13 nM.The insect injection experiment showed that the peptideκ-CTx-btg02 could effectively kill Tenebrio molitor,with a half lethal dose of 15.6 nM.The results of the electrophysiological experiment showed that 10μM peptideκ-CTx-btg02 had no blocking activity on murine acetylcholineα2β3 andα3β4.Therefore,the peptideκ-CTx-btg02 had a good inhibitory effect on the growth of insect cells,highly effective insecticidal activity and weak mammalian toxicity.[Conclusions]This study lays a foundation for the development of new,safe and efficient peptide biological insecticides. 展开更多
关键词 peptide solid phase peptide synthesis Oxidative folding Insecticidal activity ELECTROPHYSIOLOGY
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Solid-phase Synthesis of PNA Monomer by Ugi Four-component Condensation Reaction 被引量:2
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作者 WenHaoWANG XiaoMinZOU XinZHANG YiQiuFU PingXU 《Chinese Chemical Letters》 SCIE CAS CSCD 2005年第5期585-588,共4页
Peptide nucleic acids (PNA) oligomers were synthesized in most cases by peptide synthesis from N-protected monomers. In this work a new method of obtaining PNA monomer by Ugi four-component condensation reaction was t... Peptide nucleic acids (PNA) oligomers were synthesized in most cases by peptide synthesis from N-protected monomers. In this work a new method of obtaining PNA monomer by Ugi four-component condensation reaction was tested by solid-phase synthesis. The Fmoc protected PNA monomer was build up with thymin-1-yl acetic acid, 3-methylbutyl aldehyde, Fmoc protected aminoethyl isocyanide and Gly-Wang resin. 展开更多
关键词 peptide nucleic acids (PNA) Ugi four-component condensation reaction (U-4CR) solid-phase synthesis Isocyanide.
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Solid-phase Synthesis of-Haloaldehydes from Polymer-supported 4-(Phenylseleno)morpholine
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作者 ShouRiSHENG LuLingWU XianHUANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第5期456-458,共3页
Polystyrene-supported 4-(phenylseleno)morpholine was synthesized and could be used as an efficient ?selenenylating agent for saturated aldehydes. ?Haloaldehydes were prepared by reaction of polystyrene-supported ?sel... Polystyrene-supported 4-(phenylseleno)morpholine was synthesized and could be used as an efficient ?selenenylating agent for saturated aldehydes. ?Haloaldehydes were prepared by reaction of polystyrene-supported ?selenoaldehydes with bromine or sulfuryl chloride in good yield and high purity. 展开更多
关键词 solid phase organic synthesis (4-phenylseleno) morpholine -selenoaldehyde - haloaldehyde.
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Solid-Phase Stereoselective Synthesis of (E)-1, 2-Disubstituted Ethenes from Polymer-Sopported a-Selenoaldehydes
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作者 ShouRiSHENG LuLingWU XianHUANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第10期991-992,共2页
Reaction of polymer-supported a-selenoaldehydes with Grignard reagents afforded polymer-bound B-hydroxyalkyl selenides, which treated with thionyl chloride and triethylamine leading to (E)-1, 2-disubstituted ethenes i... Reaction of polymer-supported a-selenoaldehydes with Grignard reagents afforded polymer-bound B-hydroxyalkyl selenides, which treated with thionyl chloride and triethylamine leading to (E)-1, 2-disubstituted ethenes in good yield. 展开更多
关键词 solid phase organic synthesis a-selenoaldehyde (E)-1 2-disubstituted ethene.
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Solid-phase Synthesis of Unsaturated β-Dicarbonyl Compounds from Polymer-supported 4-(Phenylseleno)morpholine
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作者 Xiao Ling LIU Xing Cong WANG +1 位作者 Shou Ri SHENG Xian HUANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第9期1009-1010,共2页
The solid-phase synthesis of unsaturated ?dicarbonyl compounds has been reported.
关键词 solid phase organic synthesis 4-(phenylseleno)morpholine α-formylcycloanone unsaturated β-dicarbonyl compound.
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Preparation and Insecticidal Activity of Sea Anemone Peptide AP-GI from Aiptasia pallida
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作者 Jinxing FU Yanling LIAO +1 位作者 Xuefeidan LIU Bingmiao GAO 《Agricultural Biotechnology》 CAS 2021年第1期49-52,共4页
[Objectives] This study was conducted to synthesize sea anemone peptide Ap-GI and investigate its insecticidal activity. [Methods] The linear peptide Ap-GI was synthesized by solid phase peptide synthesis(SPPS), and t... [Objectives] This study was conducted to synthesize sea anemone peptide Ap-GI and investigate its insecticidal activity. [Methods] The linear peptide Ap-GI was synthesized by solid phase peptide synthesis(SPPS), and the linear peptide was subjected to the two-step oxidative folding, mass spectrometry identification and high performance liquid chromatography(HPLC) purification. Then, the MTT method and insect injection method were used to study its insecticidal activity. [Results] The synthesized sea anemone peptide had a purity of 95%. The test results of the MTT method showed that the peptide Ap-GI had the activity of inhibiting the growth of insect cells sf9 with the median effective dose of 0.7 nM;and the test results of the injection method on yellow mealworms showed that the peptide Ap-GI had high insecticidal activity, and the median lethal dose was 16.9 nM. [Conclusions] The sea anemone peptide Ap-GI from Aiptasia pallida has a good inhibitory effect on the growth of insect cells and high-efficiency insecticidal activity, which can lay a foundation for the development of new, safe and efficient peptide biological insecticides. 展开更多
关键词 Aiptasia pallida Sea anemone peptide solid phase peptide synthesis Oxidative folding Insecticidal activity
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Synthesis of Peptoid Nucleic Acid with Thymine as Nucleic Base
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作者 Yun WU Jie Cheng XU Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032 《Chinese Chemical Letters》 SCIE CAS CSCD 2000年第9期771-774,共4页
The synthesis of peptoid nucleic acid bearing thymine as nucleobase has been achieved. This modified oligonucleotide showed good hybridization with DNA.
关键词 PEPTOID peptide nucleic acid solid phase synthesis THYMINE
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USE OF HOEC ACTIVE ESTERS IN SOLIDPHASE PEPTIDE SYNTHESIS——THE SYNTHESIS OF GROWTH HORMONE RELEASING PEPTIDE
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作者 薛楚标 李崇熙 +1 位作者 邢其毅 董明辉 《Chinese Science Bulletin》 SCIE EI CAS 1989年第1期43-48,共6页
N-hydroxysuccinimide (HOSU) active esters have gained wide application in peptide synthesis, especially in the synthesis of longer peptides by segment conden sation, for they can avoid racemization during coupling pro... N-hydroxysuccinimide (HOSU) active esters have gained wide application in peptide synthesis, especially in the synthesis of longer peptides by segment conden sation, for they can avoid racemization during coupling processes. However, the HOSU active ester method is prone to side reactions, forming undesirable by-products such as succinimide-oxycarbonyl-alanine N-hydroxysuccinimide ester (Ⅰ) in activating steps and compound (Ⅱ) in the coupling steps sterically hindered by amino acids (proline, valine, isoleucine, etc.). 展开更多
关键词 active ESTERS solid-phase peptide synthesis N-hydoxy-exo-1 4 -epoxy-5-cyclohexene-2 3-dicarboximlde growth hormone RELEASING peptide Momany peptide.
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An Improved Synthesis of Laminin Fragment CR9
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作者 Gui Jie TIAN Shi Jun LI De Xin WANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2002年第12期1154-1157,共4页
Laminin nonapeptide CR9 was synthesized via two different methods. A notably enhanced yield (46.8%) was obtained from method B compared to that (12.4%) from standard protocol (method A).
关键词 solid-phase peptide synthesis MBHA resin Pac resin.
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一种灯盏花乙素-多肽的工艺研究
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作者 丁文锋 罗培 +7 位作者 孙新林 刘钦洲 观富宜 刘子建 彭晏 程世超 孙兴欢 蒋舟 《广州化工》 CAS 2023年第10期38-40,57,共4页
对灯盏花乙素-HomoArg-Gly-Asp-Trp-NH_(2) 的合成进行工艺研究。采用Fmoc固相合成法合成目标多肽。由于灯盏花乙素中含有多个酚羟基,粗肽在裂解时很大概率会被氧化,氧化杂质将增加粗肽纯化的难度并影响收率。对裂解体系及纯化条件进行... 对灯盏花乙素-HomoArg-Gly-Asp-Trp-NH_(2) 的合成进行工艺研究。采用Fmoc固相合成法合成目标多肽。由于灯盏花乙素中含有多个酚羟基,粗肽在裂解时很大概率会被氧化,氧化杂质将增加粗肽纯化的难度并影响收率。对裂解体系及纯化条件进行研究,结果发现,采用3-巯基丙酸/TFA/Tis/H_(2) O裂解体系及特定的洗脱梯度,可以获得纯度98%以上的目标多肽。通过工艺研究,确定了目标多肽的裂解体系和洗脱梯度,提高了纯化效率和总体产率,为相似结构的合成和产业化提供了参考。 展开更多
关键词 多肽 固相合成 RGD 灯盏花乙素 工艺研究
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Fmoc(9-芴甲氧羰基)法固相合成胸腺五肽 被引量:12
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作者 欧阳嘉 李鑫 +1 位作者 潘宗敏 沈树宝 《南京工业大学学报(自然科学版)》 CAS 2005年第3期61-64,共4页
采用对碱敏感的Fmoc法α-氨基保护策略固相合成了胸腺五肽,并讨论了胸腺五肽不同固相载体、不同活化试剂对胸腺五肽固相合成的影响。试验结果表明Fmoc合成策略中各步的缩合率均在90%以上,同时对产品进行色谱分析,纯度达到83%。
关键词 胸腺五肽 固相合成 甲氧羰基 FMOC 保护策略 Α-氨基 固相载体 试验结果 色谱分析 试剂 缩合
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虎纹捕鸟蛛毒素-Ⅰ-(HWTX-Ⅰ)28肽类似物的化学合成与活性鉴定 被引量:12
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作者 廖黔宁 罗静初 +2 位作者 周培爱 顾孝诚 梁宋平 《中国生物化学与分子生物学报》 CAS CSCD 1999年第5期756-761,共6页
虎纹捕鸟蛛毒素-(huwentoxin-,HWTX-)是从我国虎纹捕鸟蛛毒素中分离纯化得到的一种多肽类神经毒素.该多肽分子由33个氨基酸残基组成,含三对二硫键.其一级结构和三级结构均已测定.弄清该毒素的活性部位,是研究其结构功能关系的基础.用固... 虎纹捕鸟蛛毒素-(huwentoxin-,HWTX-)是从我国虎纹捕鸟蛛毒素中分离纯化得到的一种多肽类神经毒素.该多肽分子由33个氨基酸残基组成,含三对二硫键.其一级结构和三级结构均已测定.弄清该毒素的活性部位,是研究其结构功能关系的基础.用固相Fmoc化学合成的方法,合成了虎纹捕鸟蛛-的28肽类似物.该突变体去掉了天然毒素分子N端的Alal和C端的Lys30-Trp31-Lys32-Leu33共5个残基.用氧化还原型谷胱甘肽法完成二硫键配对,并用HPLC进行纯化,所得突变体与天然HWTX-的紫外光谱相似.质谱鉴定确认合成产物正确,分子量为3124,浓度为1×10-5g/ml的突变体能可逆阻断小白鼠膈神经-膈肌的接头传递,阻断时间为60~70min.与天然毒素比较,活性有所下降.结果说明HWTX-的N端、C端残基对其生物活性有一定影响,但不是位于活性中心的重要残基.由结果推测。 展开更多
关键词 虎纹捕鸟蛛毒素 固相多肽 合成 活性 蜘蛛毒素
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液相色谱-串联质谱分析化学合成多肽及其主要副产物(英文) 被引量:11
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作者 王贤纯 陈平 梁宋平 《中国生物化学与分子生物学报》 CAS CSCD 北大核心 2003年第5期576-581,共6页
用与反相高效液相色谱偶联的串联质谱 (RPHPLC MS MS)分析一个固相化学合成的九肽H2 N Tyr Val Asn Val Asn Met Gly Leu Lys CONH2 及其 2个主要的副产物 .根据Fmoc化学 ,在Fmoc PAL PEG·PS树脂上从C端至N端手工操作逐步偶联合成... 用与反相高效液相色谱偶联的串联质谱 (RPHPLC MS MS)分析一个固相化学合成的九肽H2 N Tyr Val Asn Val Asn Met Gly Leu Lys CONH2 及其 2个主要的副产物 .根据Fmoc化学 ,在Fmoc PAL PEG·PS树脂上从C端至N端手工操作逐步偶联合成九肽 .偶联完成后 ,用试剂R(90 %TFA ,5 %苯甲硫醚 ,3%二巯基乙烷 ,2 %苯甲醚 )室温 (2 0~ 2 5℃ )处理 2 5h ,进行多肽的去保护和切除树脂 .RP HPLC分析结果表明 ,合成粗品中含有 1个主要成分、2个次要成分及多个微量成分 .用RPHPLC MS MS分别对主要成分和 2个次要成分进行了鉴定 .结果证明 ,主要成分即为目标九肽 ;先于目标肽洗脱的副产物分子量比目标肽的分子量多 16 .MS MS证明 ,该副产物包括 2种九肽衍生物 :1种为其Tyr1氧化生成 ,另 1种为Met6氧化生成 ;后于目标肽洗脱的副产物为九肽的Tyr1残基增加 12所致 ,这种现象尚未见报道 . 展开更多
关键词 液相色谱-串联质谱分析 化学合成 多肽 副产物 固相合成
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虎纹捕鸟蛛毒素-Ⅰ突变体K3A-HWTX-Ⅰ的化学合成与生理活性分析 被引量:11
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作者 王贤纯 梁宋平 罗泽民 《生命科学研究》 CAS CSCD 1998年第2期87-92,102,共7页
采用固相Fmoc法在自制自动蛋白质化学工作站上合成了其第3位赖氨酸(K3)被丙氨酸(A)取代的虎纹捕鸟蛛毒素-Ⅰ的突变体K3A-HWTX-Ⅰ.合成的突变体用Edman降解和电喷雾质谱进行鉴定.K3A-HWTX-Ⅰ经谷... 采用固相Fmoc法在自制自动蛋白质化学工作站上合成了其第3位赖氨酸(K3)被丙氨酸(A)取代的虎纹捕鸟蛛毒素-Ⅰ的突变体K3A-HWTX-Ⅰ.合成的突变体用Edman降解和电喷雾质谱进行鉴定.K3A-HWTX-Ⅰ经谷胱甘肽系统进行氧化复性后通过离子交换和反相HPLC纯化.活性分析结果表明,K3被A取代后HWTX-Ⅰ的生物活性下降了80%。 展开更多
关键词 蜘蛛 虎纹捕鸟蛛毒素 突变体 固相多肽合成
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转铁蛋白受体亲和肽衍生物的制备
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作者 于家乐 李松涛 赵桂琴 《化学与生物工程》 CAS 北大核心 2024年第1期33-35,62,共4页
以2-氯三苯甲基氯(2-CTC)树脂为固相载体、N-芴甲氧羰基(Fmoc)保护氨基酸为原料、N,N′-二异丙基碳二亚胺(DIC)和1-羟基苯并三唑(HOBt)为缩合剂,采用Fmoc固相合成法制备了一种转铁蛋白受体亲和肽(transferrin receptor binding peptide,... 以2-氯三苯甲基氯(2-CTC)树脂为固相载体、N-芴甲氧羰基(Fmoc)保护氨基酸为原料、N,N′-二异丙基碳二亚胺(DIC)和1-羟基苯并三唑(HOBt)为缩合剂,采用Fmoc固相合成法制备了一种转铁蛋白受体亲和肽(transferrin receptor binding peptide,TfRBP)衍生物,其纯品的HPLC纯度为97.9%,总收率为40.3%,经ESI-MS鉴定其相对分子质量与理论值一致。该方法操作简便、合成周期短、总收率高,为进一步构建TfR靶向多肽-药物偶联物奠定了基础。 展开更多
关键词 转铁蛋白受体 固相合成 多肽 衍生物
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虎纹捕鸟蛛毒素-I单残基突变体R20 A-HWTX-I的化学合成与性质分析 被引量:8
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作者 王贤纯 梁宋平 罗泽民 《生物工程学报》 CAS CSCD 北大核心 2000年第4期490-494,共5页
虎纹捕鸟蛛毒素 Ⅰ (Huwentoxin Ⅰ ,HWTX Ⅰ )是从虎纹捕鸟蛛 (Selenocosmiahuwena)的粗毒中分离出的一种多肽类神经毒素。为了探明该毒素分子中唯一的Arg残基与其生物学活性的关系 ,运用固相多肽合成技术和Fmoc化学直接构建了Ala取代... 虎纹捕鸟蛛毒素 Ⅰ (Huwentoxin Ⅰ ,HWTX Ⅰ )是从虎纹捕鸟蛛 (Selenocosmiahuwena)的粗毒中分离出的一种多肽类神经毒素。为了探明该毒素分子中唯一的Arg残基与其生物学活性的关系 ,运用固相多肽合成技术和Fmoc化学直接构建了Ala取代HWTX Ⅰ第 2 0位Arg(R2 0 )的突变体R2 0A HWTX Ⅰ ;将合成的突变体置于含谷胱甘肽的缓冲体系中氧化复性后用反相和特殊设计的离子交换HPLC纯化 ,并对之进行氨基酸组成、Edman降解与质谱分析。活性测定结果表明 ,HWTX Ⅰ分子中的R2 0被A取代后 ,活性下降了 92 % ,提示R2 0是与活性密切相关的重要残基。 展开更多
关键词 虎纹捕鸟蛛毒素- 突变体 蛋白质工程 化学合成
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