• Microbiology and Biotechnology Letters
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• v.2 no.1
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• pp.45-50
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• 1974

1 With cysteinedesulfhydrase (E. C.4.4.1.1.) from Aerobactor aerogenes, an enzyme which catalyzes the stoichiometric conversion of L-cysteine to pyruvate, ammonia and sulfide, reversibility of the degradation of L-cysteine was investigated. It was found that the enzyme also catalized the reverse reaction of $\alpha$, $\beta$-elimination to synthesize L-cysteine derivatives from pyruvate, ammonia and sulfides when large amounts of substrates were added to the reaction mixtures. 2. The synthetic reaction by cysteinedesulfhydrase proceeded linearly with incubation time and enzyme concentrations. The optimal pH for the synthetic reaction was 10.0. 3. The results of the isolation and identification of the products showed that the L-cysteine derivatives synthesized by this enzymatic method were identical with S-methyl-L-cysteine and S-ethyl-L-cysteine respectively.

• Food preservation and processing industry
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• v.7 no.1
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• pp.33-44
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• 2008

마늘의 저장 중 생리활성과 향미에 중요한 영향을 미치는 성분의 변화를 발표된 논문을 중심으로 정리하여 살펴보았다. 또한 마늘의 냄새를 최소화하고 생리활성을 극대화할 수 있는 기능성식품의 소재개발 타당성을 살펴보기 위하여 열처리(blanching)로 마늘 중의 효소를 모두 불활성화 시킨 후, 이에 마늘로부터 추출한 alliinase를 가하여 반응조건에 따른 alk(en)yl thiosulfinates 생성 및 이들의 분해산물인 휘발성 황함유화합물의 함량변화를 측정하였다. 수확한 마늘의 최종 저장물질로 알려진 -glutamyl-S-alk(en)yl-L-cysteines는 마늘중에 존재하는 -glutamyl-transpeptidase 및 oxidase의 작용에 의하여 감소한 반면 S-alk(en)yl cysteine sulfoxide는 감소한 만큼 증가하였으며, 이는 $-3^{\circ}C$ 및 실온($23^{\circ}C$)에서 보다도 냉장온도($4^{\circ}C$)에서 가장 많이 변화하는 것으로 나타났다. 이러한 감소 및 증가현상은 -glutamyl-S-(2-popenyl)-L-cysteine이 -glutamyl-S-(trans-1-propenyl)-L- cysteine이나 -glutamyl-S-methyl-L-cysteine보다 더 컸다. -glutamyl-S-(2-propen yl)-L-cysteine은 $4^{\circ}C$에서 저장 60일 만에 66%가 감소한 반면 이로부터 생성된 S-(2- popenyl)-L-cysteine sulfoxide는 그 만큼 증가하였다. -glutamyl-S-(trans-1-propenyl)-L-cysteine 및 -glutamyl-S-methyl-L-cysteine도 $4^{\circ}C$에서 150일간 저장한 경우 각각 81% 및 39%가 감소하고, 이들로부터 각각 생성된 S-(trans-1- propenyl)-L-cysteine sulfoxides 및 S-methyl-L-cysteine sulfoxide는 증가하였다. 한편 열처리 마늘에 alliinase를 가하여 함황화합물을 재생성 시킨 결과 8종의 S-alk(en)yl cysteine sulfoxides를 확인할 수 있었다. S-(2-propenyl)-L-cysteine sulfoxide은 전체 thiosulfinates함량의 약 60%를 차지하는 것으로 나타났다. 100, 200, 300 및 400 unit의 alliinase를 첨가하여 15분간 반응시킨 결과 총 thiosulfinates는 생마늘(대조구)에 비하여 각각 37, 68, 77 및 80%가 생성되는 것으로 나타났다. GC/MSD를 이용하여 대조구 및 효소를 첨가하여 반응시킨 시료의 휘발성 향기성분을 분석한 결과 alliinase를 100, 200, 300 및 400 unit 첨가하여 15분간 반응시키면 각각 마늘의 휘발성 향기성분이 25, 36, 66및 76% 씩 재 생성되는 것으로 나타났다. 이상의 결과를 종합해 볼 때 마늘을 이용한 제품개발이나 연구를 할 경우 마늘의 저장조건에 따른 생리활성물질의 분석결과를 근거로 하여 이루어져야 하며, 또한 효소를 이용하여 적절히 반응시키면 마늘 냄새를 $30{\sim}80%$ 범위 내에서 조절이 가능한 것으로 나타났다.

• Bulletin of the Korean Chemical Society
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• v.2 no.4
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• pp.125-129
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• 1981

The addition reactions of cysteine without blocking amino and carboxyl groups to substituted and unsubstituted ${\beta}$-nitro-styrene derivatives were investigated. ${\beta}$-Nitrostyrene(1a), p-methyl-${\beta}$-nitrostyrene(1b), 3,4,5-trimethoxy-$[\beta}$ -nitrostyrene(1c), $[\varpi}$-3,4-methylenedioxy-${\beta}$ -nitrostyrene(1d), o-, m- and p-chloro-${\beta}$ -nitrostyrene (1e, 1f, 1g) and o-, m- and p-methoxy-${\beta}$-nitrostyrene (1h, 1i, 1j) easily undergo addition reactions with cysteine to form S-(2-nitro-1-phenylethyl)-L-cysteine(3a), S-[2-nitro-1-(p-methyl)phenyl-ethyl]-L-cysteine(3b), S-[2-nitro-1-(3',4',5'-trimethoxy) phenylethyl]-L-cysteine(3c), S-[2-nitro-1-($[\vatpi}$ -3',4'-methylenedioxy)phenylethyl]-L-cysteine(3d), S-[2-nitro-1-(o-chloro)phenylethyl]-L-cysteine(3e), S-[2-nitro-1-(m-chloro)-phenylethyl]-L-cysteine(3f), S-[2-nitro-1-(p-chloro)phenylethyl]-L-cysteine(3g), S-[2-nitro-1-(o-methoxy)phenylethyl]-L-cysteine(3h), S-[2-nitro-1-(m-methoxy)phenylethyl]-L-cysteine(3i) and S-[2-nitro-1-(p-methoxy)phenylethyl]-L-cysteine(3j), respectively. The structure of adducts were confirmed by means of UV-spectrum, IR-spectrum, molecular weight measurement and elemental analysis. The various factors effecting the yield of cysteine adducts to ${\beta}$-nitrostyrene derivatives were also studied.

• The Korean Journal of Food And Nutrition
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• v.23 no.3
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• pp.361-367
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• 2010

In this study, cysteine compounds found in genus Allium plants, including N-acetyl cysteine(NAC), S-allyl cysteine(SAC), S-ethyl cysteine(SEC), and S-methyl cysteine(SMC), were examined for effects on blood glucose, glucose tolerance, and plasma lipid concentrations in streptozotocin(STZ)-induced diabetic mice. In the mice, the ingestion of these cysteine compounds did not affect blood glucose levels significantly. However, their ingestion did improve the diabetic symptoms of polydipsia, polyphagia, polyuria, and weight loss. Glucose tolerance was also found to be improved in the STZ diabetic animals by feeding the cysteine compounds. Treatment of the compounds also caused a slight decrease in plasma concentrations of total cholesterol along with increases in HDL-cholesterol and slight decreases in LDL-cholesterol, resulting in a significant decrease in the atherogenic index of plasma in the diabetic animals. They also showed reductions of liver triglyceride content to relieve diabetic fatty liver syndrome. In summary, the cysteine compounds such as NAC, SAC, SEC, and SMC, found in genus Allium plants, had certain beneficial effects on blood glucose metabolism along with preventing abnormalities in lipid metabolism, a complication of diabetes, by improving the atherogenic index of plasma and fatty liver in STZ-induced diabetic mice.

• Bulletin of the Korean Chemical Society
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• v.11 no.3
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• pp.251-253
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• 1990

L-Alanine(L-ala) and S-methyl-L-cysteine(L-mcy) cobalt(III) complexes of a flexible $N_2O_2$-type tetradentate ligand ethylenediamine-N,N'-di- -butyric acid(eddb), s-cis-[Co(eddb)(L-ala)] and s-cis-[Co(eddb)(L-mcy), have been prepared via the substitution reactions of the s-cis-$[Co(eddb)Cl_2]$-complex with, respectively, L-alanine and S-methyl-L-cysteine. Both L-alanine and S-methyl-L-cysteine are found to coordinate to the cobalt(III) ion via the nitrogen and oxygen donor atoms to give the meridional s-cis isomer. Electronic absorption, ir and pmr spectra are used to characterize the complexes obtained in this work along with elemental analysis data.

• Journal of the Korean Chemical Society
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• v.33 no.5
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• pp.516-521
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• 1989

Reaction between the $N_2O_2-type$ tetradentate ligand, ethylenediamine-N,N'-di-S-${\alpha}$-isobutylacetic acid (SS-emiba) and $RhCl_3{\cdot}3H_2O$ has yielded ${\Delta}-s-cis-\;and\;{\wedge}-uns-cis-[Rh(SS-eniba)Cl_2]-$. ${\Delta}-s-cis-[Rh(SS-eniba)Cl_2]^-$ has been utilized to react with S-methyl-L-cystcine(Smc) to give ${\Delta}-s-cis-[Rh(SS-eniba(Smc)]^+$. The oxidation of ${\Delta}-s-cis-[Rh(SS-eniba(Smc)]^+$ using $H_2O_2$ has produced ${\Delta}-s-cis-[Rh(SS-eniba)(Smc-o)]^+$, in which the coordinated sulfur has been converted into the sulfoxide group. In a separate series of experiments the S-methyl-L-cysteine is oxidized by $H_2O_2$ to give S-methyl-L-cysteine sulfoxide, which is then coordinated to ${\Delta}-s-cis-[Rh(SS-eniba)Cl2]^-$ to make the standard complet of ${\Delta}-s-cis-[Rh(SS-eniba)(Sme-o)]+$ for comparison with the complex obtained from the oxidation of ${\Delta}-s-cis-[Rh(SS-eniba)(Smc)]^+\;by\;H_2O_2.$

• Bulletin of the Korean Chemical Society
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• v.9 no.3
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• pp.115-117
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• 1988

The addition of L-cysteine without blocking amino and carboxyl groups to${\beta},{\beta}$-dinitrostyrene derivatives(11a-e) were investigated. ${\beta},{\beta}$ -Dinitrostyrene derivatives(11a-e) easily undergo addition reactions with L-cysteine to from s-(2,2-dinitro-1-phenylethyl)-L-cysteine(12a), s-[2,2-dinitro-1-(p-methyl)phenylethyl]-L-cysteine (12b), s-[2,2-dinitro-1-(p-methoxy)phenylethyl]-L-cystein e(12c), s-[2,2-dinitro-1-(p-chloro)phenylethyl]-L-cysteine (12d) and s-[2,2-dinitro-1-(p-nitro)phenylethyl]-L-cysteine( 12a), respectively. The structure of adducts were confirmed by means of spectral data, molecular weight measurement and elemental analysis.

• Proceedings of the Korean Society for Applied Microbiology Conference
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• 1986.12a
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• pp.515.1-515
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• 1986

Thermostable tryptophanase was extracted from a thermophilie bacterium, strain T which was absolutely symbiotic with strain 5. The enzyme was purified 14.7 fold with 5.8% yield by chromatographies using ion exchange, gel filtration, and hydrophobic interaction columns, followed by high performance liquid chromatography on hydroxyapatite column. The purified enzyme has a molecular weight of approximately 210,000 estimated by gel filtration column chromatography, and the molecular weight of subunit was determined by SDS polyacrylamide gel electrophoresis to be 46,000, which indicates that the native enzyme is made of four homologous subunits. The tryptophanase was stable at 65o0 and the optimum temperature for the enzyme activity for 20 min reaction was 70$^{\circ}C$. The purified enzyme activity for 20 min ieaction was 70$^{\circ}C$. The purified enzyme catalyzed the degradation of L-tryptophan into indole, pyruvate and ammonia in the presence of pyridoxal phosphate. 5-Hydroxy-Ltryptophan, 5-methyl-DL-tryptophan, L-cysteine, S-methyl-L-cysteine, 5-methyl-DL-tryptophan, L-cysteine, S-methyl-Lcysteine, and L-serine were also used as substrates to form pyruvate. The amino acid composition of the tryptophanase was determined, and found to contain a high percentage of hydrophobic amino acids, especially in the proline content, which was much higher than that of Escherichia coli tryptophanase. In addition, the 35N-terminal amino acid sequence of the tryptophanase was completely different from that of E. coli tryptophanase.

• Bulletin of the Korean Chemical Society
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• v.23 no.6
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• pp.851-856
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• 2002

The Reaction of S-methyl-S-cysteine(L-Smc) with racemic $s-cis-[Co(demba)Cl_2]-1$ (Hydmedba = $NN'-dimethylethylenediamine-NN'-di-\alpha-butyric$, acid) yields ${\Delta}$-s-cis-[Co(dmedba)(L-Smc)] 2 with N, O-chelation. Oxidation of sulfur of 2 with $H_2O_2$ in a 1 : 1 mole ratio gives ${\Delta}$-s-cis[Co(dmedba)(L-S(O)mc)] 3 having an uncoordinated sulfenate group. Oxidation of sulfur of L-Sm with $H_2O_2in$ a 1: 1 mole ratio produces S-methyl-L-cysteinesulfenate (L-S(O)me) 5. Direct reaction of 1 with 5 in basic medium gives an N.O-chelated ${\Delta}$s-cis[Co(dmedba)(L-S(O)mc)-N.O], which turmed out be same as obtained by oxidation of 2, while an N, S-chelated ${\Delta}$-s-cis-[Co(dmedba)(S-S(O)mc)-N,O] complex 4 is obtained in acidic medium from the reaction of 1 with 5. This is one of the rare $[$Co^{III}$(N_2O_2-type$ ligand)(amino acid)] type complex preparations, where the reaction conditions determine which mode of N, O and N, S caelation modes is favored.

• Bulletin of the Korean Chemical Society
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• v.11 no.4
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• pp.354-357
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• 1990

Synthesis of dichloro cobalt (Ⅲ) complexes of a flexible $N_2O_2-type$ tetradentate ligand, ethylenediamene-N,N'-di-${\alpha}$-isobutyric acid (eddib), has yielded two geometrical isomers, s-cis-$(Co(eddib)Cl_2)- and uns-cis-(Co(eddib)Cl_2)-.$ A series of substitution reactions, $(Co(eddib)Cl_2)^- {\to} (CO(eddib)Cl H_2O) {\to} (Co(eddib)CO_3)^- {\to} (Co(eddib(H_2O)_2)^+$ have been run for each of the two geometrical isomers. The reaction between the s-cis-(Co(eddib)Cl_2)^-$ complex and L-alanine (L-als) or S-methyl-L-cysteine (L-mcy) gave the meridional s-cis-[Co(eddib)(aa)) (aa = L-ala or L-mcy) complex. The S-methyl-L-cysteine was found to coordinate to cobalt (Ⅲ) ion via the nitrogen and oxygen donor atoms.