Synthetic Studies on Penems and Carbapenems(IV). Practical Preparation of (3R,4R)-4-Acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one Derivatives from 6-Aminopenicillanic Acid

Goo, Yang-Mo,Lee, Young-Bok,Kim, Ho-Hyun,Lee, Youn-Young,Lee, Woo-Young Korean Chemical Society 1987 Bulletin of the Korean Chemical Society Vol.8 No.1

Preparation of optically pure (3R, 4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-o ne derivatives, which can be employed as starting materials for synthesis of carbapenem and penem antibiotics, was established in high efficiency from 6-amino-penicillanic acid (6-APA). 6-APA was diazotized and brominated to give 6, 6-dibromopenicillanic acid and its methyl ester was metalated with methylmagnesium bromide and condensed with acetaldehyde. The product, methyl 6-bromo-6-(1-hydroxyethyl)penicillanate was reduced with Zn-$NH_4Cl-NH_4OH$-acetone efficiently to give methyl 6-(l-hydroxyethyl)-penicillanate, which was protected either with ${\beta},{\beta},{\beta}$ -trichloroethoxycarbonyl group or with t-butyldimethylsilyl group. The thiazolidine rings of these compounds were cleaved by treatment of mercury(II) acetate in acetic acid and permangante in acetone in sequence to afford the desired optically pure final products.

Resistance of Kanamycin- and Neomycin-Producing Streptomycetes to Aminoglycoside Antibiotics

Goo, Yang-Mo,Choi, Seok-Rye,Kim, Kyung-Ja Korean Chemical Society 1994 Bulletin of the Korean Chemical Society Vol.15 No.7

Streptmyces fradiae NRRL B1195 and Streptomyces kanamyceticus IFO 13414 are highly resistant to the antibiotics they produce. The ribosomes of these organisms are found to be susceptible to the antibiotics, but the cell free extract of S fradiae is found to contain a phosphotransferase and an acetyltransferase which inactivate kanamycin and neomycin, and that of S. kanamyceticus an acetyltransferse which inactivates kanamycin and neomycin. The resistance of these organisms against streptomycin is found to be due to the resistant ribosomes; actually streptomycin activates their ribosomal systems for the synthesis of polyphenylalanine.

Effects of Natural Selection, Mutagenesis, and Protoplast Formation and Cell Wall Regeneration on the Production of Aminoglycoside Antibiotics

Goo, Yang-Mo,Lim, Hyon-Joo,Lim, Seok-Ran,Kim, Kong-Hwan,Lim, Bun-Sam,Lee, Sae-Bae The Pharmaceutical Society of Korea 1989 Archives of Pharmacal Research Vol.12 No.4

High producers or blocked mutants of aminoglycoside antibiotic-producing Streptomyces spp. were selected by application of an agar plug method and by culturing individual colonies in broth. The productivities of aminoglycoside antibiotic producing organisms were increased by selection of a high producer from colonies obtained by spreading spores of wild strain, or survived from treatment of a mutagen or from the colonies regenerated from protoplast-formation and cell-wall regenerations. Some mutagen treated colonies lost the ability to produce antibiotics (5-8%). Some A-factor negative and deostreptamine or streptidine negative mutants were obtained by N-methyl-N'-nitro-N-nitrosomethylguanidine (MNNG) treatment. Many of the survivors from the MNNG treatment lost the ability to produce antibiotics. Major colonies produced less amount of antibiotics ; only few survived colonies produced more antibiotics than the parent. Resistance of Streptomyces spp. against the antibiotics produced by itself was also markedly affected by mutagen treatment.

A New Streptothricin Family Antibiotic Producing Streptomyces Spp. Snus 8810-111 ; Characterization of The Producing Organisms, Fermentation, Isolation, and Structure Elucidation of Antibioitics

Goo, Yang-Mo,Kim, Ok-Yun,Joe, Young-Ae,Lee, Young-Bok,Ju, Jeongho,Kim, Beom-Beom-Tae,Lee, Youn-Young The Pharmaceutical Society of Korea 1996 Archives of Pharmacal Research Vol.19 No.2

A new streptothricin family antibiotic producing Streptomyces spp. SNUS 8810-111 was isolated from a soil sample. Study of its morphological and physiological characters indicated that the antibiotic producing organism was a Streptomyces spp. Taxonomical studies suggested that the organism might belong to the genus streptomyces gougeroti. The organism produced antibiotics most in calcium carbonate-tryptic soy broth. The active principles were recovered from the broth with a cation exchange resin and eluted from the resin with HCI. Cellulose column chromatography gave two active principles.$^1H-^1H$ Homo-COSY study on the first compound revealed four structural components. Total hydrolysis of the antibiotic with HCI allowed isolation of $\beta-lysine$. From these data the antibiotic was found to be streptothricin D. The other compound showed one additional signal in the .$^1H$NMR and the $^{13}C$ NMR spectra. The signal was from a methyl group attached to a nitrogen atom. Comparison of the NMR signals with those of streptothricin D suggested that the compound was N-methyl-streptothricin D which was a new compound in the family of streptothricin antibiotics.

Mutasynthesis of Aminocyclitol antibiotics

Goo, Yang Mo 생화학분자생물학회 1988 BMB Reports Vol.15 No.4

Studies of genetics of antibiotic producing organiams are limited because the knowledge of gene-enzyme relationship is very little. Knowledge of gene-enzyme relationship will be accumulated by isolation and mapping of mutants blocking biosynthesis of antibiotics. Antibiotic blocked mutants at single steps in biosynthetic pathways usually do not accumulate intermediates because of the antibiotic committed enzymes' broad substrate specificity and because of the other existing enzymatic actions on the intermediate to produce the same kinds of antibiotics in mutants. In many antibiotic producing organiams, many intermediates involved in activation and polymerization reactions and some are probably enzyme bound and hence are not free to accumulate in the medium. The active sites of antibiotic committed enzymes are typically less accessible to exogenously added substrates than the corresponding sites of enzymes in primary metabolism. Many antibiotic committed enzymes are subject to inactivation or facile dissociation upon extraction, or subject to proteases. Mutasynthesis of antibiotics, by using antibiotic blocked mutants are one of the genetic application of antibiotic producing organisms to develop new antibiotics and to understand the biosynthetic pathways of antibiotics. Many aminocyclitol antibiotics produced by various Streptomyces sps. and Micromonospora sps. have some subunits in molecules, such as deoxystrepamine in neomycins, parmomycins, lividomycins, ribostamycin, xylostasin, butirosins, kanamycin, tobramycin, seldomycins, gentamycins and hygromycins, streptidine in streptomycins, bluensidine in bluensomycin, actinamine in spectiomycin and monoaminocyclitols in validamycins, minosaminomycin and hygromycin. Many blocked mutants of these antibtotic producing organisms were obtained by mutation with UV or nitrosoguanidine treatment. The mutants are characterized by the inability to biosynthesize aminocyclitols which are part of the antibiotics produced by the parent organisms. If aminocyclitols are not supplied in media, they can not produce the corresponding antibiotics. Many Dmutants were isolated and studied to develop new antibiotics by feeding mutasynthons. This method was very successful to evaluate the biosynthetic pathways for aminocyclitol antibiotics. Following this antibiotic blocked mutant study, neomycins are to be biosynthesized from 2-deoxystreptamine to neamine, to ribostamycin and to neomycins in sequence. Physiological genetic evidence support that plasmids may carry one or more genes that either code for antibiotic committed enzymes or regulate the expression of such enzymes. The study of the antibiotic blocked mutants will eventually allow to establish the genetics of antibiotic producing organisms, their control mechanisms and their application to industry.

항생물질 생산 토양 Actinomycetes 균주 선별과 항생물질 생산특성 조사

구양모(Yang Mo Goo),이윤영(Youn Young Lee),정연숙(Youn Sook Chung),이영복(Young Bok Lee),조영애(Young Ae Joe),조희영(Hee Yeong Cho),고영선(Young Sun Koh),이창훈(Chang Hoon Lee) 대한약학회 1991 약학회지 Vol.35 No.3

Selective culture of actinomycetes from soil microbes and their antibiotic producing characters by agar-disk method were examined. Some of the organisms which produced antibiotics on agar disk did not produce antibiotics in liquid culture. Further examination indicated that production of antibiotic was dependent on the composition of medium. Many streptomycestes produced antibacterial substances in tryptic soy broth but others produced antifungal antibiotics in V-8 broth. Production of antibacterial substances by Streptomyces sp. was also dependent on the medium composition.

곰팡이균 , 이스트 , 스트렙토마이쎄테스와 박테리아의 나이트릴기 가수분해 효소들에 관한 연구 α - 아미노 페닐아세토나이트릴의 나이트릴기를 가수분해시키어 페닐글라이신을 얻는 생화학적 방법의 개발

구양모 ( Yang Mo Goo ) 생화학분자생물학회 1986 BMB Reports Vol.19 No.1

When α-aminophenylacetonitrile was fed to fungi, yeast, Streptomycetes, or bacteria growing in nutrient and Theriault`s media, most of them were found to accumulate phenylglycine in the media. Some of them, A. unguis, A. oryzae, P. purpurogenum, B. spectabilis, B. subtilis, E. coli, and R. rubra cultured in the nutrient media, and P. varioti, B. spectabilis, G. subo.xydans, R. glutinis, and R. toruloides cultured in the Theriault`s media showed accumulation of phenylglycine in a large quantity. It was found that, when the organisms were examined by a cell contact method for the converion of the substrate to phenylglycine by incubation of the substrate with harvested cells in a buffer for 5 hrs, P. digitatum, B. spectabilis, and R. toruloides grown in the Theriault`s media and B. spectabilis, R. glutinis, and R. toruloides grown in the nutrient medium showed strong nitrite group hydrolyzing enzymes` activity when they were induced by the substrate. Most of them did not show any conversion of the substrate to phenylglycine or phenylglycineamide without preinduction except A. gigantus, A. flaviple, A. panamensis, P. varioti, E. coli, P. vulgaris, P. aeruginosa, and R. toruloides. Also, no microorganisms examined in this experiment showed production of phenylglycineamide before or after pre-induction in the culture or in the cell contact media.

The Reaction of Carbenes Formed by Decomposition of the Diazo Group in $\beta$- or $\gamma$-Position in 4-Alkylthioazetidin-2-one Derivatives

Yang, Jae-Moon,Wang, Han-Cheol,Lee, Youn-Young,Goo, Yang-Mo Korean Chemical Society 1992 Bulletin of the Korean Chemical Society Vol.13 No.1

噴霧耕栽培에서 栽培時期에 따른 감자 秀美(Superior), 大地(Dejima) 및 男爵(lrish cobbler) 品種의 生長과 塊莖形成

梁承烈,丁蓮圭,梁元模,姜宗求 順天大學校 農業科學硏究所 1996 農業科學硏究 Vol.10 No.-

This study was carried out to investigate the effects of growing season on growth and tuberization of potato(Solanum tuberosum L.) cv. Superior, Dejima and Irish cobbler grown in aeroponic system. Plant height and fresh weight of shoot and stolon were greater in summer season(Planting date May 15, Harvesting date Jul. 16) than those in winter season(Planting date Jan. 14, Harvesting date Mar. 16), regardless of cultivars. However, number of tubers per plant was decreased in summer season regardless of cultivars. Especially, tuber formation of cv. Dejima was significantly inhibited and secondary growth of the buds of tubers initiated in summer season.

養液栽培商品의 生産과 流通實態 및 改善方向

姜宗求,梁承烈,梁元模 順天大學校 農業科學硏究所 1993 農業科學硏究 Vol.7 No.-

To illuminate the state and countermeasure of soilless cultural production and marketing in Korea, the survey of soilless cultural production through Agricultural Agent Center, questionnaire, field investigation, and literature analysis were performed. Soilless cultural farm-houses were 82 and area was 11.1 ㏊ on September, 1992. But its area of chief producing district and kind of crops are rapidly being changed. To solve the problems of soilless culture in Korea; old age and low education of farmers, small cultural area, financial difficulty, none standardization of facilities material and none specialization of varieties for soilless culture, it must be actively put in practice for soilless cultural improvement of Korea that the technical education strengthenning, financial support by government, standardization of facilities material and variety specialization. Poor sales network and policy, poor marketing intelligence network and activities, negligent selection and packing of products become the major cause of soilless culture's failure. Therefore, spontaneous sales network organization, marketing support of Horticultural Cooperative Association and Agricultural Cooperative Association, elevation of marketing intelligence power, and continuous effort of farmer for successful selection and packing of products are essential factors for soilless cultural development of Korea. Soilless culture is a royal road to change from primary agriculture to secondary agriculture for agricultural innovation, but there are many problems in this system and it is difficult to solve that problems by only farmer's effort. Therefore, not only farmer but also researcher, scholar, related groups and government concentrate their effort on solution of soilless cultural problems.