• Title/Summary/Keyword: amidation

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Peptide Amidation: Production of Peptide Hormones in vivo and in vitro

  • Kim, Kyun-Hwan;Baik L. Seong
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.6 no.4
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    • pp.244-251
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    • 2001
  • Over half of all biologically active peptide and peptide hormones are $\alpha$-amidated at their C-terminus, which is essential for their full biological activities. Amidation is accomplished through the sequential reaction of the two enzymes encoded by the single bifunctional, peptidyl-glycine $\alpha$-amidating monooxygenase (PAM or an $\alpha$-amidating enzyme). PAM catalyze the forma - tion of a peptide amide from peptide precursors that include a C-terminal glycine, and requires copper molecular oxygen and ascorbate. PAM is the only enzyme that produces peptide amides in vivo. However various strategies utilizing PAM, carboxypeptidase-Y enzymes, and chemical syn-thesis have been developed for producing peptide amides in vitro. The growing need and impor-tance of peptide amide drugs has highlighted the necessity for a efficient in vitro amidating sys-tem for industrial application for the production of peptide hormones, like calcitonin and oxytocin. This review presents the current situation regarding amidation with a special emphasis on the in-dustrial production or peptide hormones.

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Effective Amidation of Carboxylic Acids Using (4,5-Dichloro-6-oxo-6H-pyridazin-1-yl)phosphoric Acid Diethyl Ester

  • Kang, Seung-Beom;Yim, Heung-Seop;Won, Ju-Eun;Kim, Min-Jung;Kim, Jeum-Jong;Kim, Ho-Kyun;Lee, Sang-Gyeong;Yoon, Yong-Jin
    • Bulletin of the Korean Chemical Society
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    • v.29 no.5
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    • pp.1025-1032
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    • 2008
  • (4,5-Dichloro-6-oxo-6H-pyridazin-1-yl)phosphoric acid diethyl ester (3a) are efficient and selective coupling agents for the amidation of carboxylic acids. Amidation of aliphatic and aromatic carboxylic acids with aliphatic and aromatic amines using 3a under mild condition gave chemoselectively the corresponding amides in good to excellent yield. Three protected-dipeptides were also synthesized from N-BOC-Phe and O-Me-amino acid hydrochlorides using 3a under mild condition.

Synthesis and Characterization of Thermo-responsive Poly(N-isopropylacrylamide) via Hydrolysis and Amidation of Poly(acrylonitrile) (폴리아크릴로니트릴의 가수분해와 아미드화에 의한 열감응성 폴리(N-이소프로필아크릴아미드)의 합성과 특성분석)

  • Lee, Hee Dong;Kim, Young Ho
    • Polymer(Korea)
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    • v.37 no.6
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    • pp.784-793
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    • 2013
  • A two-step method for obtaining poly(N-isopropylacrylamide) (PNIPAAm) from poly(acrylonitrile) (PAN) was investigated in order to find a feasibility of imparting thermo-responsive property onto textile fiber materials. PAN was converted to poly(acrylic acid) (PAA) by hydrolysis at a first-step, and then PAA was converted to PNIPAAm at a second step via an amidation reaction of PAA with isopropylamine (IPA) in DMF medium using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) as catalysts. High content of carboxylic groups at the first step was obtained by the successive alkaline and acid hydrolysis of PAN. The degree of conversion of PAA to PNIPAAm at the second step was dependent on the amount of catalysts EDC and NHS. PNIPAAm converted from PAA through amidation reaction showed a lower critical solution temperature (LCST) behavior when the conversion was higher than about 53%.

Synthesis of Antithypertensive Agents via Couping Reaction of Benzothiazepinone and 1,4-Dihydropyridine Derivatives

  • Ham, Won-Hun;Yang, Jae-Gwon;Lim, Tae-Gyun;Jung, Yun-Ho;Chung, Yun-Sung
    • Archives of Pharmacal Research
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    • v.17 no.2
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    • pp.119-123
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    • 1994
  • The synthesis of 3a, 3b, 7a fro Benzpthiazepinone and 1,4-dihyropyridine derivatives is described. Benzothiazepinone nad 1,4-dihydropyridine derivatives were prepared according to literature procedure. The key reactions involve esterification and amidation of benzothize-pinone nad 1,4-dihydropyridine derivatives.

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Effect of 1,6-Hexamethylenediamine Content on the Properties/Adhesive Strength of EVA/Itaconated EPDM Blend Foams (I) (헥사메텔렌 디아민이 EVA/Itaconated EPDM 블렌드 발포체의 물성 및 접착강도에 미치는 영향 (I))

  • Jung, Hyun-Ji;Lee, Young-Hee;Kim, Jung-Soo;Lee, Dong-Jin;Kim, Sung Yeol
    • Textile Coloration and Finishing
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    • v.30 no.2
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    • pp.107-116
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    • 2018
  • Simplification of the manufacturing process in shoe making is essential to improve productivity and reduce production costs. To improve the adhesion of EVA foam used as a midsole, EVA/itaconated EPDM(EPDM-g-IA)(80/20wt%) blend was prepared using Torque Rheometer-Plasti-Corder, and 1,6-hexamethylenediamine/crosslinking agent/foaming agent/additive were mixed, followed by amidation reaction and foaming to prepare EVA/EPDM-g-IA foam for shoe midsole. In this study, we investigate the effect of the content of 1,6-hexamethylenediamine(0, 0.5, 1.0, 2.0, 3.0) on the mechanical properties, water-contact angle and adhesion of EVA/itaconated EPDM foam. As the content of 1,6-hexamethylenediamine increased, mechanical properties such as tensile strength, tear strength, tensile elastic modulus, hardness, and water-contact angle were lowered, but elongation at break and compression set(%) were increased. Both normal type and non-UV type adhesive strength increased with increasing diamine content. In particular, it was found that the adhesion strength of the non-UV type adhesion increased sharply with increasing diamine content. As a result, an adherend rupture occurs in a foam sample having a content of 1,6-hexamethylenediamine of 3phr. From this, it can be seen that the EVA/itaconated EPDM foam for shoe midsoles, which can be used for non-UV adhesion without primer and UV treatments, have been developed.

Influence of Alkylation on Interface and Thermal Conductivity of Multi-walled Carbon Nanotubes-reinforced Epoxy Resin (알킬화가 다중벽탄소나노튜브로 강인화된 에폭시수지의 계면 및 열전도도에 미치는 영향)

  • Heo, Gun-Young;Rhee, Kyong-Yop;Park, Soo-Jin
    • Polymer(Korea)
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    • v.35 no.6
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    • pp.548-552
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    • 2011
  • Two functionalization methods, i.e., acid treatment and chemical amidation were performed to prepare the functionalized multi-walled carbon nanotubes (MWCNT), and the properties of epoxy/functionalized MWCNT composites were investigated and compared. Fourier transform infrared spectroscopy (FTIR) was used to confirm the surface functionality of the MWCNT obtained by the functionalization methods. The effects of the MWCNT functionalization on the interface and thermal conductivity were studied by zeta potential analyzer, scanning electron microscope and thermal conductivity analyzer. From these results, it was confirmed that the thermal conductivity of the epoxy/MWCNT composites could be increased by grafting with dodecylamine. This could be interpreted by relatively strong dispersion forces of the grafting MWCNT with dodecylamine in DGEBF epoxy resin. These results were in good agreement with the results that the zeta potential value of the grafting MWCNT with dodecylamine has a higher negative value than that of MWCNT with acid treatment.

Synthesis and Photophysical Properties of Bispsoralen Derivatives Linked by a Bisamide-polymethylene Chain

  • Yoo, Dong-Jin
    • Bulletin of the Korean Chemical Society
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    • v.28 no.10
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    • pp.1715-1719
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    • 2007
  • New bispsoralen derivatives 5-10, 8-MOP-NHCO(CH2)nCONH-8-MOP (BPSBA-Cn, n = 0, 1, 2, 3, 4 and 5) in which 5 position of an 8-methoxypsoralen (8-MOP) is linked by various lengths of bisamide polymethylene chain to 5 position of the other 8-MOP, have been synthesized by the amidation of 5-amino-8-methoxypsoralen (12) with α,ω-alkanoyl dichloride. Photophysical properties of their derivatives including π?π stacking interaction between the two aromatic moieties were investigated by UV absorption and fluorescence emission spectra. Efficient ring-ring stacking interactions have been observed in BPSBA-C4 (9) from the percent hypochromism (%H) of the models.

Optimization of the Optical Resolution of Racemic $\alpha$-Methylbenzylamine Catalyzed by Enzymatic Reaction in Organic Media (유기용매에서 효소반응을 통한 라세믹 $\alpha$-Methylbenzylamine 광학적 분할의 최적화)

  • 강병영;김병기
    • KSBB Journal
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    • v.9 no.3
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    • pp.306-311
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    • 1994
  • Optical resolution of racemic ${\alpha}$-methylbenzylamine was carried out by using Bacillus licheniformis protease in organic media. Enantioselective amidation of racemic amino with an ester as an acyl donor was successfully employed to resolve the racemate. To enhance reaction rate and enantioselectivity, pH-adjustment by lyophilization of enzyme dissolved in buffer, colyophilization with salts or lyoprotectants, selection of solvents and molecular design of esters were investigated. The optimization of the resolution reaction achieved about 30-fold increase in initial reaction rate and about 12-fold increase in enantioselectivity, respectively.

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