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1.
Toshifumi Miyazawa Makoto Hiramatsu Takashi Murashima Takashi Yamada 《Biotechnology letters》2002,24(23):1945-1949
The coupling between the carbamoylmethyl ester of an N-protected amino acid or dipeptide (at 25 mM) and an amino acid amide (at 100 mM) was achieved using Aspergillus melleus protease in 1,1,1,3,3,3-hexafluoro-2-propanol/N,N-dimethylformamide (1:1, v/v); the coupling efficiencies were dependent largely on the combination of amino acid residues: e.g. the dipeptide yields after 48 h were for l-Ala + Gly, 100% and for l-Leu + l-Leu, 16%. 相似文献
2.
Peptide deformylase as biocatalyst for the synthesis of enantiomerically pure amino acid derivatives
Theo Sonke Bernard Kaptein A. F. Volker Wagner Peter J. L. M. Quaedflieg Sabine Schultz Sandra Ernste Annette Schepers John H. M. Mommers Quirinus B. Broxterman 《Journal of Molecular Catalysis .B, Enzymatic》2004,29(1-6):265
Peptide deformylases (PDFs) catalyze the removal of the N-terminal formyl group from nascent polypeptides. In spite of the vast amount of literature on PDF, no information whatsoever is available on its use in organic synthesis. To be able to explore the potential of E. coli PDF (EcPDF) in biocatalytic applications, a simple and efficient purification procedure was developed. This method, which was based on one affinity chromatographic step, furnished about 200 mg of pure EcPDF from 1 L of E. coli culture. The enzyme combined a good activity (tof ≥5 s−1) with an almost complete enantioselectivity (E ratio >500) in the resolution of N-formylated α- and β-amino acids, α-amino acid amides and α-aminonitriles. N-Formyl derivatives of non-functionalized amines and β-amino alcohols were hydrolyzed with low to moderate activity and enantioselectivity. EcPDF was also successfully applied in the enantioselective formylation of α-aminonitriles, yielding, e.g. (S)-N-formyl-phenylalanine nitrile with >99.5% ee. The enzyme also proved very suitable for the mild and selective deprotection of N-formyl peptides as was shown for N-formyl-Leu-Tle-NHCH3. This deprotection increased the diastereomeric excess of the dipeptide, which was unsatisfactory because of racemization of the N-terminal amino acid in the chemical peptide coupling step. 相似文献
3.
Shi‐Jun Li Yi Zhao Yi‐Bing Huang Gui Gao Dai‐Hui Zhang Li Xu 《Preparative biochemistry & biotechnology》2013,43(2):158-171
Abstract The protease‐catalyzed, kinetically controlled synthesis of a precursor dipeptide of thymopentin(TP‐5), Z‐Arg‐Lys‐NH2 in organic solvents was studied. Z‐Arg‐OMe was used as the acyl donor and Lys‐NH2 was used as the nucleophile. An industrial alkaline protease alcalase and trypsin were used to catalyze the synthesis of the target dipeptide in water‐organic cosolvent systems. The conditions of the synthesis reaction were optimized by examining the effects of several factors, including organic solvents, water content, temperature, pH, and reaction time on the yield of Z‐Arg‐Lys‐NH2. The optimum conditions using alcalase as the catalyst are pH 10.0, 35°C, in acetonitrile/DMF/Na2CO3‐NaHCO3 buffer system (80∶10∶10, V/V), 6 h, with the dipeptide yield of 71.1%. Compared with alcalase, the optimum conditions for trypsin are pH 8.0, 35°C, in ethanol/Tris‐HCl buffer system (80∶20, V/V), 4 h, with the dipeptide yield of 76.1%. 相似文献
4.
Toshifumi Miyazawa Shino Masaki Kayoko Tanaka Takashi Yamada 《Letters in Peptide Science》2003,10(2):83-87
Bacillus subtilis protease (Amano protease N) was examined as a catalyst for peptide bond formation via both the kinetically and thermodynamically controlled approaches. In general, the latter approach proved to be superior to the former, and a series of dipeptide syntheses and several segment condensations were achieved in good to high yields using the immobilized enzyme on Celite in acetonitrile with low water content. 相似文献
5.
Miyazawa Toshifumi Masaki Shino Tanaka Kayoko Yamada Takashi 《International journal of peptide research and therapeutics》2003,10(2):83-87
Summary
Bacillus subtilis protease (Amano protease N) was examined as a catalyst for peptide bond formationvia both the kinetically and thermodynamically controlled approaches. In general, the latter approach proved to be superior to
the former, and a series of dipeptide syntheses and several segment condensations were achieved in good to high yields using
the immobilized enzyme on Celite in acetonitrile with low water content. 相似文献
6.
B. Picur M. Lisowski I.Z. Siemion 《International journal of peptide research and therapeutics》1998,5(2-3):183-187
Summary We have found that besides the known cyclolinopeptides A (CLA) and B (CLB), there is a new cyclic peptide in linseed mill
cake that we have named CLX. Its composition is very similar to that of CLA, a cyclic peptide with a distinct immunosuppressive
activity. The sequence of this peptide has been established ascyclo(PPFFILLX), where X is a non-proteinaceous amino acid,N-methyl-4-aminoproline. this amino acid substitutes for two amino acid residues of CLA, mimicking a dipeptide moiety with
a nonplanarcis amide bond. The non-proteinaceous amino acid X may mimic a transition state of the peptide bond which exists in such processes
as, e.g., PPIase-catalysedcis/trans amide-Pro bond isomerisation. 相似文献
7.
Summary Mixtures of cyclic peptides, formed by head-to-tail cyclizations of side-chain resin-bound linear sequences, have been prepared using solid-phase synthesis. Fast atom bombardment mass spectrometry of cyclic peptides with various metal ions can reveal preferred modes of host-guest patterns, albeit in a nonquantitative manner. This approach could prove useful for more rapid screening of potential peptide ionophores. A cyclic heptapeptide with a dipeptide tail proved to be a particularly effective host for a Ca2+ ion; in a small three-component mixture, cyclo[Gly-Asp-d-Pro-Xxx-Asp-d-Pro-Asp(Aca-Phe-NH2)], binding to Ca2+ varied from Xxx=N-MeAla>GlySar. In a 15-component mixture, cyclo[Pro-Xxx-Asn-Pro-Xxx-Asn] where Xxx=Ala, Glu, Leu, Lys or Phe, there were no significant differences with respect to binding to metal ions. We believe this to be the first reported use of cyclic peptide libraries for screening metal ions to discern host-guest relationships.Abbreviations Aca
aminocaproic acid
- Boc
tert-butyloxycarbonyl
- BOP
benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate
- DCM
dichloromethane
- DIEA
diisopropylethylamine
- DMF
N,N-dimethylformamide
- ESI
electrospray ionization
- FABMS
fast atom bombardment mass spectrometry
- pMBHA
4-methylbenzhydrylamine
- TFA
trifluoroacetic acid
This paper is based on a presentation given at the Symposium on Peptide Structure and Design as part of the 31st Annual ACS Western Regional Meeting held in San Diego, CA, USA, October 18–21, 1995. 相似文献
8.
Shi-Jun Li Jian-An Wang Jing Li Dan Suo 《Preparative biochemistry & biotechnology》2013,43(4):334-347
Abstract The protease-catalyzed, kinetically controlled synthesis of a precursor dipeptide, Z-Asp-Val-NH2 of thymopentin (TP-5), in organic solvents was studied. Z-Asp-OMe and Val-NH2 were used as the acyl donor and the nucleophile, respectively. An industrial alkaline protease alcalase was used to catalyze the synthesis of the target dipeptide in water-organic cosolvent systems. The conditions of the synthesis reaction were optimized by examining the effects of several factors, including organic solvents, water content, temperature, pH, and reaction time on the yield of Z-Asp-Val-NH2. The optimum conditions using alcalase as the catalyst are pH 10.0, 35°C, in acetonitrile/Na2CO3-NaHCO3 buffer system (9:1, V/V), reaction time 5 h, with a yield of 63%. The dipeptde product was confirmed by LC- MS. 相似文献
9.
Integral equation theory is applied to the determination of the intramolecular potential of mean force for the glycine dipeptide, N-acetyl glycyl-N-methylamide, in aqueous solution. The solvated free energy for the dipeptide as a function of the dihedral angles ? and ψ (Ramachandran plot) is determined and compared with the vacuum surface. Conformations forbidden in vacuum are found to be populated in aqueous solution. The results of the glycine dipeptide are compared to a parallel study on the alanine dipeptide. Solvent effects are found to be responsible for the extent of many of glycines properties related to flexibility. 相似文献
10.
Matthew P. Sarnowski Kyle P. Pedretty Nicole Giddings H. Lee Woodcock Juan R. Del Valle 《Bioorganic & medicinal chemistry》2018,26(6):1162-1166
The stabilization of β-sheet secondary structure through peptide backbone modification represents an attractive approach to protein mimicry. Here, we present strategies toward stable β-hairpin folds based on peptide strand N-amination. Novel pyrazolidinone and tetrahydropyridazinone dipeptide constraints were introduced via on-resin Mitsunobu cyclization between α-hydrazino acid residues and a serine or homoserine side chain. Acyclic and cyclic N-amino peptide building blocks were then evaluated for their effect on β-hairpin stability in water using a GB1-derived model system. Our results demonstrate the strong β-sheet stabilizing effect of the peptide N-amino substituent, and provide useful insights into the impact of covalent dipeptide constraint on β-sheet folding. 相似文献
11.
Miyazawa Toshifumi Hiramatsu Makoto Murashima Takashi Yamada Takashi 《International journal of peptide research and therapeutics》2002,9(4-5):173-177
Summary The couplings ofN-protected amino acid esters with amino acid amides proved to be carried out in anhydrous acetonitrile in the presence ofBacillus licheniformis protease (subtilisin Carlsberg) immobilized on Celite. The maximal peptide yields were obtained with the immobilized enzyme
prepared through lyophilization from a pH 10.7 buffer solution. A series of dipeptide syntheses and several segment condensations
were achieved generally in high yields by the combined use of the immobilized enzyme prepared from this pH and the carbamoylmethyl
ester as the acyl donor. 相似文献
12.
Toshifumi Miyazawa Makoto Hiramatsu Takashi Murashima Takashi Yamada 《Letters in Peptide Science》2002,9(4-5):173-177
The couplings of N-protected amino acid esters with amino acid amides proved to be carried out in anhydrous acetonitrile in the presence of Bacillus licheniformis protease (subtilisin Carlsberg) immobilized on Celite. The maximal peptide yields were obtained with the immobilized enzyme prepared through lyophilization from a pH 10.7 buffer solution. A series of dipeptide syntheses and several segment condensations were achieved generally in high yields by the combined use of the immobilized enzyme prepared from this pH and the carbamoylmethyl ester as the acyl donor. 相似文献
13.
Summary Two series of inverse substrates,m-guanidinophenyl andm-(guanidinomethyl)phenyl esters derived fromN-(tert-butyloxycarbonyl)amino acid, were prepared as an acyl donor component for trypsin-catalyzed peptide synthesis. The kinetic behavior of these esters toward tryptic hydrolysis was analyzed. They were found to couple with an acyl acceptor such asl-alaninep-nitroanilide to produce dipeptide in the presence of trypsin.Streptomyces griseus trypsin was a more efficient catalyst than the bovine trypsin. Within the enzymatic peptide coupling methods, this approach was shown to be advantageous, since the resulting peptides are resistant to the enzymatic hydrolysis.Abbreviations Boc
tert-butyloxycarbonyl
- Aib
-aminoisobutyric acid
- DMSO
dimethylsulfoxide
- Tris
tris(hydroxymethyl)aminomethane
- MOPS
3-morpholino-l-prop anesulfonate
- G
guanidinophenyl
- GM
(guanidinomethyl)phenyl
-
pNA
p-nitroanilide 相似文献
14.
Mechanism of osmotically regulated N-acetylglutaminylglutamine amide production inRhizobium meliloti
Rhizobium meliloti adapts to environments of high osmolarity by accumulating glutamate, trehalose, and the dipeptide N-acetylglutaminylglutamine amide (NAGGN) intracellularly. In this study, the mechanism of NAGGN production and accumulation was examined. NAGGN was produced in osmotically shocked cultures after a lag period of more than one hour, and NAGGN was undetectable in cultures treated with chloramphenicol, indicating that genetic induction is required for NAGGN accumulation.In vitro radiolabeling experiments demonstrated that the peptide synthesis step in NAGGN production did not occur ribosomally. Rather, it was catalyzed by an ATP-dependent enzyme that appeared to be both induced by high osmolarity and activated by K+. Also, a mutant analysis suggested that NAGGN may be partly responsible for the osmotic tolerance observed inR. meliloti. 36% of mutants that were characterized as osmotically sensitive compared to the parent strain, were also found to contain reduced levels of NAGGN. The phenomenon of osmolyte accumulation as it relates to adaptation to other environmental stresses is discussed. 相似文献
15.
In order to study the secretion of the human urokinase-type plasminogen activator, u-PA, from the yeastYarrowia lipolytica, three kinds of integrative expression vector were constructed. These vectors differed only in their secretion control regions,
pre-, pre-dip- (dipeptide stretch) or pre-dip-pro sequences of the alkaline extracellular protease, which were joined inframe
to the human u-PA cDNA. The recombinantY. lipolytica strains, transformed with the expression vectors, secreted the hyperglycosylated u-PA. A fibrin plate assay of the culture
supernatants showed that the hyperglycosylated u-PA proteins could catalyze fibrinolysis, and that the pre-dip sequence was
the most efficient secretory signal for the secretion of the u-PA fromY. lipolytica. This result suggests thatY. lipolytica can be developed as a potential host for the production of recombinant human u-PA. 相似文献
16.
Mitsunobu Sakajoh Nadine A. Solomon Arnold L. Demain 《Journal of industrial microbiology & biotechnology》1987,2(4):201-208
Summary Bacilysin, a dipeptide antibiotic produced byBacillus subtilis A 14, was synthesized by a cell-free extract of the producing organism from its constitutent amino acids,l-alanine andl-anticapsin. The synthesis required ATP and Mg2+ and was optimal at pH 8.1. The same extract also synthesizedl-alanyl-l-alanine. The synthesis of bacilysin was not inhibited by chloramphenicol, DNase or RNase. 相似文献
17.
R. Bruce Martin 《Biopolymers》1998,45(5):351-353
For every n amino acids linked in a protein there are n − 1 peptide bonds. The free energy of peptide bond hydrolysis and formation in aqueous solution defines the equilibrium position between peptide and amino acid hydrolysis products. Yet few experimental values exist. With a minimum of assumptions, this paper deduces the free energies of hydrolysis of a variety of peptide bonds. Formation of a dipeptide from two amino acids is about eight times more difficult than subsequent condensations of an amino acid to a dipeptide or longer chain. Condensation of an amino acid to a peptide of any size is five times more difficult than joining two smaller peptides of at least dipeptide size. Thus in an abiogenesis scenario there is a kind of nucleation in peptide bond formation with the initial condensation of two amino acids to yield a dipeptide more difficult than subsequent condensations to a growing chain. © 1998 John Wiley & Sons, Inc. Biopoly 45: 351–353, 1998 相似文献
18.
Summary A new and convenient method for synthesizing norstatine derivatives has been developed. The key step is the preparation of propargylic alcohols from N-Fmoc or N-Boc amino aldehydes, followed by transformation to carboxylic acids after protection of the alcohols. The N-Boc-protected derivatives are coupled to a dipeptide sequence to afford peptide mimetics (norstatines). 相似文献
19.
Several Streptomyces species cause plant diseases, including S. scabies, S. acidiscabies and S. turgidiscabies, which produce common scab of potato and similar diseases of root crops. These species produce thaxtomins, dipeptide phytotoxins
that are responsible for disease symptoms. Thaxtomins are produced in vivo on diseased potato tissue and in vitro in oat-based
culture media, but the regulation of thaxtomin biosynthesis is not understood. S. acidiscabies was grown in a variety of media to assess the impact of medium components on thaxtomin A (ThxA) production. ThxA biosynthesis
was not correlated with bacterial biomass, nor was it stimulated by α-solanine or α-chaconine, the two most prevalent potato
glycoalkaloids. ThxA production was stimulated by oat bran broth, even after exhaustive extraction, suggesting that specific
carbohydrates may influence ThxA biosynthesis. Oat bran contains high levels of xylans and glucans, and both of these carbohydrates,
as well as xylans from wheat and tamarind, stimulated ThxA production, but not to the same extent as oat bran. Starches and
simple sugars did not induce ThxA production. The data indicate that complex carbohydrates may act as environmental signals
to plant pathogenic Streptomyces, allowing production of thaxtomin and enabling bacteria to colonize its host. 相似文献
20.
《Bioorganic & medicinal chemistry letters》2020,30(15):127283
We report the parallel synthesis of gramicidin S derivatives featuring backbone N-amino substituents. Analogues were prepared by incorporation of N-amino dipeptide subunits on solid support. Nine backbone-aminated macrocycles were evaluated for growth inhibitory activity against ESKAPE pathogens and hemolytic activity against human red blood cells. Diamination of the Orn residues in the β-strand region of gramicidin S was found to enhance broad-spectrum antimicrobial activity without a corresponding increase in hemolytic activity. 相似文献