• Title/Summary/Keyword: solid phase peptide synthesis

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Synthesis of Cyclic Antifreeze Glycopeptide and Glycopeptoids and Their Ice Recrystallization Inhibition Activity

  • Ahn, Mija;Murugan, Ravichandran N.;Shin, Song Yub;Kim, Eunjung;Lee, Jun Hyuck;Kim, Hak Jun;Bang, Jeong Kyu
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3565-3570
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    • 2012
  • Until now, few groups reported the antifreeze activity of cyclic glycopeptides; however, the tedious synthetic procedure is not amenable to study the intensive structure activity relationship. A series of N-linked cyclic glycopeptoids and glycopeptide have been prepared to evaluate antifreeze activity as a function of peptide backbone cyclization and methyl stereochemical effect on the rigid Thr position. This study has combined the cyclization protocol with solid phase peptide synthesis and obtained significant quantities of homogeneous cyclic glycopeptide and glycopeptoids. Analysis of antifreeze activity revealed that our cyclic peptide demonstrated RI activity while cyclic glycopeptoids showed no RI activity. These results suggest that the subtle changes in conformation and Thr orientation dramatically influence RI activity of N-linked glycopeptoids.

Synthesis of Dermorphin Analogues by the Solid Phase Method and Biological Activity (고상법에 의한 Dermorphin 유사체의 합성과 생물학적 활성에 관한 연구)

  • Han, Man-So
    • Journal of the Korean Applied Science and Technology
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    • v.19 no.4
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    • pp.281-290
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    • 2002
  • Dermorphin is a hepta peptide(H-Tyr-DAla-Phe-Gly-Tyr-Pro-Ser-$NH_{2}$)with exceptionally potent and long-lasting peripheral and central activity. Dermorphin analogues, dermorphionyl(DMP)-Lys-$NH_{2}$ and DMP-Lys-Lys-$NH_{2}$ have been prepared in order to examine the effect of opiod activity. Dermorphin analogues were synthesized by the solid phase method. The crude peptide was purified by gel filter on a Sephadex LH-20, characterized with HPLC and amino acid analyzer. Analgesic potency was estimated by writhing syndrome method and Randall-Selitto method. As a result, dermorphin analogues have lower potency than that of morphine.

Chemical Synthesis and Cloning of Panax ginseng Peptide Gene

  • Zhang, Hong-Ying;Chen, Dong-Song;Zhang, Jin
    • Proceedings of the Ginseng society Conference
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    • 1990.06a
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    • pp.65-67
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    • 1990
  • The sequence of ginseng peptide gene was designed and synthesized by the solid phase plasmid pUC19. Escherichia coli JM101 cells were transformed with above hybrid plasmids. Ampicillin resistant transformants were screened and identified by in situ colony hybridization and Southern blot techinques. Finally the gene sequencing was done by the Sanger dideoxy method using primer extension.

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Chemical Synthesis and Cloning of Panax ginseng Peptide Gene (인삼펩티드 유전자의 합성 및 클로닝)

  • Zhang, Hong-Ying;Chen, Dong-Song;Zhang, Jin
    • Journal of Ginseng Research
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    • v.14 no.2
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    • pp.207-209
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    • 1990
  • The sequence of ginseng peptide gene was designed and synthesized by the solid phase phosphoramidiate method. Synthetic segments were isolated, pllrified and joined to the plasmid pUC19. E.icherichiu coli JM101 cells were transformed with above hybrid plasmids. AmpiciIBin resistant transformants were screened and identified by in situ colony hybridization and Southern blot techniques. Finally the gene sequencing was done by the Sanger dideoxy method using primer extension.

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A novel nicotinoyl peptide, nicotinoyl-LVH, for collagen synthesis enhancement in skin cells

  • Kim, Hyoung Shik;Ryu, Seung Hwan;Kim, Hye In;Cho, Seung Hee;Lee, Jeong Hun;Han, Byung Suk;Lee, Kyung Rok;Moh, Sang Hyun
    • Journal of Applied Biological Chemistry
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    • v.59 no.3
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    • pp.239-242
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    • 2016
  • A novel Nicotinoyl fused peptide, Nicotinoyl-LVH, was synthesized by solid phase peptide synthesis method, purified, and tested in cultured skin cells. Nicotinoyl-LVH enhanced the expression level of collagen mRNA and its fragments in fibroblasts. These data show that this novel Nicotinoyl peptide is a promising biomaterial in the anti-aging functional cosmetic market.

PEGylation of Silk Fibroin Model Peptide

  • Kweon, Hae-Yong;Jo, You-Young;Yeo, Joo-Hong;Woo, Soon-Ok;Han, Sang-Mi;Lee, Kwang-Gill
    • International Journal of Industrial Entomology and Biomaterials
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    • v.20 no.2
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    • pp.87-91
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    • 2010
  • Silk fibroin model peptide, alanine pentamer was synthesized through solid-phase method and modified with poly(ethylene glycol). Nuclear magnetic resonance spectrometry and Fourier-transform infrared spectroscopy showed the conformation of alanine pentamer, $\beta$-sheet structure and random coil conformation were not changed with PEGylation. Differential scanning calorimetry showed that relatively strong exothermic peak around $180^{\circ}C$ by PEGylation. No cytotoxicity of PEGylated pentamer was observed by L929 cell proliferation test.

Peptide Synthesis with Polymer Bound Active Ester. Ⅱ. Synthesis of Pyrazolone Resin and Its Application in Acylation Reaction

  • Jong-Bum Kim;Yoon-Sik Lee
    • Bulletin of the Korean Chemical Society
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    • v.12 no.4
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    • pp.376-379
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    • 1991
  • Pyrazolone group containing resin was tested as an acyl carrier in solid phase peptide synthesis. Several kinds of dipeptide derivatives were prepared by aminolysis reactions of Boc-amino acid-pyrazolone resin active ester with various carboxyl protected amino acid derivatives. It was found that the rates of aminolysis reactions were largely dependent on the bulkiness of the amino acid side chains, the carboxyl protecting groups, and the swelling property of the resin. All the dipeptide derivatives were obtained in high yield in 20-30 minutes, and the pyrazolone resin could be reused repeatedly in peptide synthesis without any change of its reactivity.

Synthesis of Halicylindramide A Mimetics Containing Lactone Isosteres

  • Yeo, Sang-Hyuk;Seo, Hyun-Ju;Lim, Dong-Yeol
    • Bulletin of the Korean Chemical Society
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    • v.32 no.spc8
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    • pp.2916-2920
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    • 2011
  • Synthesis of halicylindramide A mimetics via solid-phase peptide synthesis is described. The N-Me-Gly-Thr residues in halicyclindramide A has been replaced by N-Me-Gly-Dpr, Lys, or N-Me-Gly-allo-Thr. Solution structures of the mimetics were compared by CD spectroscopy in an aqueous buffer and in TFE.

Synthesis of 3β [L-Lysinamide-carbamoyl] Cholesterol Derivatives by Solid-Phase Method and Characteristics of Complexes with Antisense Oligodeoxynucleotides

  • Lee, Eun-Jung;Lee, Min-hyung;Park, Jong-Sang;Choi, Joon-Sig
    • Bulletin of the Korean Chemical Society
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    • v.27 no.7
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    • pp.1020-1024
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    • 2006
  • In this report, we describe the synthesis of mono- and di-valent cationic $3\beta$ [L-Lysinamide-carbamoyl] cholesterol (K-Chol) derivatives by solid-phase peptide synthesis method and the characteristics of K-Chol/antisense oligodeoxynucleotide (ODN) complexes. K-Chol was able to interact with antisense ODNs electrostatically and constructed nanometer-sized complexes of 50-100 nm in diameter. The formation of K-Chol/antisense ODN complexes was demonstrated by non-denaturing polyacrylamide gel electrophoresis assay and atomic force microscopy. The cell-associated radioactivity was measured to monitor the cellular uptake of the complexes containing radioactive antisense ODNs using HL 60 cells.

Synthesis of Small Molecule-Peptide Conjugates as Potential Whitening Agents

  • Lee, Hye-Suk;Shin, Kyong-Hoon;Ryu, Geun-Seok;Chi, Gyeong-Yup;Cho, In-Shik;Kim, Han-Young
    • Bulletin of the Korean Chemical Society
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    • v.33 no.9
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    • pp.3004-3008
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    • 2012
  • Small molecule conjugated peptides were prepared by solid-phase synthesis as potential novel whitening agents, and their melanogenesis inhibitory activities were investigated. The conjugated small molecules were well-known materials as tyrosinase inhibitors, and peptides were selected from the sequences that are known to antagonize melanocortin receptor 1 (MC1R). Most of small molecules-peptide conjugates showed superior melanin inhibition activity to kojic acid and arbutin. Among these, almost all compounds have -AR- sequence. From this study, we concluded that the small molecule conjugated peptides containing -AR- sequence have melanogenesis inhibitory activities and have potential to be used as novel whitening agents.