CN1557961A - Biologic preparation method of cyclic dipeptide analogue compound and uses thereof - Google Patents
Biologic preparation method of cyclic dipeptide analogue compound and uses thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 36
- 108010016626 Dipeptides Proteins 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims description 9
- 125000004122 cyclic group Chemical group 0.000 title abstract 3
- 241000196324 Embryophyta Species 0.000 claims abstract description 22
- 244000237956 Amaranthus retroflexus Species 0.000 claims abstract description 14
- 235000013479 Amaranthus retroflexus Nutrition 0.000 claims abstract description 13
- 230000001717 pathogenic effect Effects 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 235000015097 nutrients Nutrition 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 241000589636 Xanthomonas campestris Species 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
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- 230000001580 bacterial effect Effects 0.000 claims description 8
- 239000002054 inoculum Substances 0.000 claims description 8
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- 230000035772 mutation Effects 0.000 claims description 7
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- 244000292693 Poa annua Species 0.000 claims description 5
- 238000009333 weeding Methods 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 240000005373 Panax quinquefolius Species 0.000 claims description 4
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- 108010080698 Peptones Proteins 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- -1 aliphatic amino acid Chemical class 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 4
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- 238000011081 inoculation Methods 0.000 claims description 4
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- 239000002244 precipitate Substances 0.000 claims description 4
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- 238000010025 steaming Methods 0.000 claims description 4
- 239000006228 supernatant Substances 0.000 claims description 4
- 238000004809 thin layer chromatography Methods 0.000 claims description 4
- 244000201986 Cassia tora Species 0.000 claims 1
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Abstract
The present invention is several kinds of cyclic dipeptide compounds prepared with pathogenic redroot amaranth variant of wild rape xanthomonas in the preservation number of CGMCC No. 0902 and with high efficiency herbicidal activity, and through fermentation, separation and purification. The process of the present invention is simple, practical, low in cost, high in yield and pollution-less and suitable for industrial production, and the prepared cyclic dipeptide compounds has high herbicidal activity on redroot amaranth, goose foot and other weeds.
Description
Technical field
The present invention relates to the biological preparation method and the purposes of known CYCLIC DIPEPTIDES compounds.
Background technology
CYCLIC DIPEPTIDES compounds all has discovery in people, animal, plant, fungi and bacterium, the ring dipeptides that structure is different, its biological function significant difference, specifically include suppress weeds, regulate calcium channel, antibiotic, single-minded catalysis steric configuration and as the biological activitys such as signaling molecule of bacterium physiological regulating control.Therefore, CYCLIC DIPEPTIDES compounds has huge potentiality to be exploited at the aspects such as development of medicine, microbiotic and agricultural biological weedicide.
Domestic have scientific research institutions of a few family in the research and development of carrying out CYCLIC DIPEPTIDES compounds, and the Zhou Shining of Zhongshan University etc. separate from South Sea mangrove fungi and marine bacteria fermented liquid and are purified to the ring dipeptide compound; Open Wang of research laboratory of Chinese Academy of Sciences Kunming vegetable chemistry has obtain 3 ring dipeptides and promptly encircle (bright-dried meat), ring (phenylpropyl alcohol-different bright) and encircle (phenylpropyl alcohol-bright) the elementary separation from the Schisandra chinensis fruit; The Tao Lin of Bengbu Medical College etc. synthesize ring L-phenylpropyl alcohol-L-dried meat with chemical process; Kunming Inst. of Botany, Chinese Academy of Sciences's vegetable chemistry and the western plant resources Xiong Jiang of National Key Laboratory etc. are separated to CYCLIC DIPEPTIDES compounds from the ethanol extraction of many stamens Radix Phytolaccae.
External more active to the research of CYCLIC DIPEPTIDES compounds, mainly concentrate in the bioactive discussion, Yasuo kimura etc. from penicillium sp., separate obtain the ring (L-look-L-phenylpropyl alcohol), studies show that its energy strongly inhibited Chinese celery seed germination under 100ml/l, promote the growth of lettuce root; Milne, P.J. wait and studied 4 ring dipeptide compound rings (L-phenylpropyl alcohol-L-dried meat), ring (L-junket-L-dried meat), ring (L-look-L-dried meat) and rings (L-look-L-look), the result shows that these 4 ring dipeptide compounds all have the anti-muscular tone of potential, anti-knurl and antibiotic activity; Holden, Matthew T.G. etc. from the pseudomonas fermented liquid, separate obtain 2 the ring dipeptide compound rings (D-third-L-figured silk fabrics), the ring (L-junket-L-dried meat), studies show that noclilucence is played the Signal Regulation effect.
Since the nineties in last century, CYCLIC DIPEPTIDES compounds research is begun to turn to bacterium, but obtain CYCLIC DIPEPTIDES compounds and at home and abroad still belong to the first time from the xanthomonas campestris Amaranthus retroflexus extraction separation purifying that causes a disease the mutation fermented liquid; And it is simple and feasible to extract the CYCLIC DIPEPTIDES compounds method from this fermented liquid, low than the chemosynthesis cost.
Summary of the invention
The objective of the invention is to based on Microbiological Principle, with separate from rhizosphere soil or plant tissue the mutation of causing a disease of xanthomonas campestris Amaranthus retroflexus be bacterial classification, through fermentation, separate, purify, obtain CYCLIC DIPEPTIDES compounds; Further biological activity test shows that this compounds has strong restraining effect to part weeds and paddy rice.Therefore, the starting point of the present invention is that the plant malignant bacteria with new screening is that bacterial classification has extensive bioactive CYCLIC DIPEPTIDES compounds and the application in weed control thereof with biological method preparation.
The biological preparation method of CYCLIC DIPEPTIDES compounds of the present invention (formula 1),
cyclo-(-A
1-A
2-)
(formula 1)
Wherein, A1 is Pro, Phe, Leu, a kind of aliphatic amino acid or a kind of die aromatischen Aminosaeuren;
A2 is Try, Phe, Ile, a kind of aliphatic amino acid or a kind of die aromatischen Aminosaeuren;
It is characterized in that may further comprise the steps:
1) with deposit number be: the pathogenic mutation (Xanthomonas campestris pv.retroflexus) of the high-performance bio weeding bacterium xanthomonas campestris Amaranthus retroflexus of CGMCC NO.0902 is a bacterial classification, in conventional solid medium, this bacterial classification is carried out slant culture, rejuvenation is cultivated 9-24h for 25-30 ℃; Carry out seed culture then, contain the liquid nutrient medium of 2/3 volume in the 400ml triangular flask, the prescription of liquid nutrient medium is: extractum carnis 0.5-2.2%, peptone 0.2-4%, glucose 0.2-4%, NH4H2PO40.05-0.5%, NaCl0.1-2.0% supplies volume with water; Accent initial p H6.0-7.4, at the 121-125 ℃ of 20-30min that sterilizes down, the cooling back is inoculated with 1% inoculum size, cultivates 12-32h for 25-30 ℃.
2) liquid nutrient medium of Sheng 2/3 volume in the fermentor tank, the prescription of liquid nutrient medium are with the prescription of above-mentioned seed liquor body substratum, and with the inoculum size inoculation of 6-12%, air flow is 1 by volume: 0.6-1.5, cultivate 54-120h for 25-30 ℃, and get fermented liquid;
3) the centrifugal supernatant liquor concentrating under reduced pressure that gets of fermented liquid, repeatedly precipitate the removal polysaccharide with acetone, pressure reducing and steaming acetone, left liquid pH is transferred to 3-7, with isopyknic ethyl acetate extraction several, combined ethyl acetate extracting solution then, be concentrated into its underpressure distillation dried, with the dissolve with methanol of 1-5 milliliter, separate with silicagel column, with sherwood oil: ethyl acetate is the gradient elution from 10: 1 to 4: 6 by volume; The part of triketohydrindene hydrate colour developing behind the hydrochloric acid hydrolysis is separated with silicagel column, component after the thin layer chromatography analysis that character is identical merges, and makes CYCLIC DIPEPTIDES compounds again.
The present invention has the following advantages:
1. separate being purified to CYCLIC DIPEPTIDES compounds from fermented liquid with biological method, with respect to chemosynthesis, its method is simple and feasible, and environment is not polluted;
2. from fermented liquid, separate being purified to CYCLIC DIPEPTIDES compounds with biological method, with respect to chemosynthesis, its cycle short (being generally circulation in 5-7 days); Raw materials used cheapness is easy to form large-scale mass production, and production cost is low;
3. be that strain fermentation is produced CYCLIC DIPEPTIDES compounds with the pathogenic mutation (Xanthomonascampestris pv.retroflexus) of high-performance bio weeding bacterium xanthomonas campestris Amaranthus retroflexus, it is higher that part is encircled the dipeptides productive rate;
The performance of this CYCLIC DIPEPTIDES compounds has stronger biological activity, can be used for being developed to being campelyco.
Description of drawings
Fig. 1 is biological preparation technology's schema of CYCLIC DIPEPTIDES compounds;
Fig. 2 is the biology inhibition determination of activity figure of ring (dried meat-phenylpropyl alcohol-) to roots of plants;
Fig. 3 is the biology inhibition determination of activity figure of ring (dried meat-phenylpropyl alcohol-) to axis;
To be ring (different bright-phenylpropyl alcohol-) suppress determination of activity figure to the biology of roots of plants to Fig. 4;
To be ring (different bright-phenylpropyl alcohol-) suppress determination of activity figure to the biology of axis to Fig. 5;
Fig. 6 is the biology inhibition determination of activity figure of ring (Se-phenylpropyl alcohol-) to roots of plants;
Fig. 7 is the biology inhibition determination of activity figure of ring (Se-phenylpropyl alcohol-) to axis.
Embodiment
Embodiment 1: the biology preparation of CYCLIC DIPEPTIDES compounds
1) with pathogenic mutation (Xanthomonascampestris pv.retroflexus) bacterial classification of high-performance bio weeding bacterium xanthomonas campestris Amaranthus retroflexus, carry out slant culture in conventional solid medium, rejuvenation is cultivated 24h for 25 ℃; Carry out seed culture then, contain the liquid nutrient medium of 2/3 volume in the 400ml triangular flask, the prescription of liquid nutrient medium is (by the mass/volume ratio): extractum carnis 2.2%, peptone 0.4%, glucose 0.2%, NH
4H
2PO
40.5%, NaCl2.0% supplies volume with water; Accent initial p H value is 6.0, and at 121 ℃ of 20min that sterilize down, the cooling back is inoculated with 1% inoculum size, cultivates 32h for 25 ℃.
2) liquid nutrient medium of Sheng 2/3 volume in the fermentor tank, the prescription of liquid nutrient medium are with the prescription of above-mentioned seed liquor body substratum, and with 10% inoculum size inoculation, air flow is 1: 1.5 by volume, cultivates 120h for 27 ℃, gets fermented liquid;
3) the centrifugal supernatant liquor that gets of fermented liquid, concentrating under reduced pressure, acetone repeatedly precipitates the removal polysaccharide, pressure reducing and steaming acetone transfers to 7 with left liquid pH, with isopyknic ethyl acetate extraction three times, last underpressure distillation is concentrated into dried, with 4 milliliters dissolve with methanol, separate with silicagel column, with sherwood oil: ethyl acetate is the gradient elution from 10: 2 to 4: 6 by volume; The part silicagel column separation and purification that according to a conventional method triketohydrindene hydrate behind the hydrochloric acid hydrolysis is developed the color again, component after the thin layer chromatography analysis that character is identical merges, get 8 components, through gas, liquid chromatography, mass spectrum, nuclear magnetic resonance spectroscopy turns out to be ring (dried meat-phenylpropyl alcohol-), ring (different bright-phenylpropyl alcohol-), ring (Se-phenylpropyl alcohol-), ring (dried meat-Se-), ring (dried meat-bright-), ring (phenylpropyl alcohol-phenylpropyl alcohol-), ring (dried meat-junket-), ring, and (Se-Se), wherein the content of ring (dried meat-phenylpropyl alcohol-), ring (different bright-phenylpropyl alcohol-) reaches 200mgL respectively
-1And 100mgL
-1With 10 tons fermentor tanks is example, fermentation once, through separation and purification can be respectively pure ring (dried meat-phenylpropyl alcohol-) and encircle (different bright-phenylpropyl alcohol-) each 1.5kg and 0.8kg.
Embodiment 2: the biology preparation of CYCLIC DIPEPTIDES compounds
1) with pathogenic mutation (Xanthomonascampestris pv.retroflexus) bacterial classification of high-performance bio weeding bacterium xanthomonas campestris Amaranthus retroflexus, carry out slant culture in conventional solid medium, rejuvenation is cultivated 24h for 25 ℃; Carry out seed culture then, contain the liquid nutrient medium of 2/3 volume in the 400ml triangular flask, the prescription of liquid nutrient medium is: extractum carnis 0.5%, peptone 0.2%, glucose 0.5%, NH
4H
2PO
40.05%, NaCl0.5% supplies volume with water; Accent initial p H value is 6.0, and at 121 ℃ of 20min that sterilize down, the cooling back is inoculated with 1% inoculum size, cultivates 28h for 25 ℃.
2) liquid nutrient medium of Sheng 2/3 volume in the fermentor tank, the prescription of liquid nutrient medium are with the prescription of above-mentioned seed liquor body substratum, and with 6% inoculum size inoculation, air flow is 1: 0.6 by volume, cultivates 100h for 25 ℃, gets fermented liquid;
3) the centrifugal supernatant liquor that gets of fermented liquid, concentrating under reduced pressure, acetone repeatedly precipitates the removal polysaccharide, pressure reducing and steaming acetone transfers to 7 with left liquid pH, with isopyknic ethyl acetate extraction three times, last underpressure distillation is concentrated into dried, with 5 milliliters dissolve with methanol, separate with silicagel column, with sherwood oil: ethyl acetate is the gradient elution from 9: 2 to 5: 5 by volume; The part silicagel column separation and purification that according to a conventional method triketohydrindene hydrate behind the hydrochloric acid hydrolysis is developed the color again, component after the thin layer chromatography analysis that character is identical merges, get 8 components, through gas, liquid chromatography, mass spectrum, nuclear magnetic resonance spectroscopy turns out to be ring (dried meat-phenylpropyl alcohol-), ring (different bright-phenylpropyl alcohol-), ring (Se-phenylpropyl alcohol-), ring (dried meat-Se-), ring (dried meat-bright-), ring (phenylpropyl alcohol-phenylpropyl alcohol-), ring (dried meat-junket-), ring, and (Se-Se), wherein the content of ring (dried meat-phenylpropyl alcohol-), ring (different bright-phenylpropyl alcohol-) reaches 100mgL respectively
-1And 50mgL
-1With 10 tons fermentor tanks is example, fermentation once, through separation and purification can be respectively pure ring (dried meat-phenylpropyl alcohol-) and encircle (different bright-phenylpropyl alcohol-) each 0.8kg and 0.4kg.
Embodiment 3: the plant growth inhibiting activity of ring (dried meat-phenylpropyl alcohol-) is measured
With weeds and accelerating germination of rice seed such as Amaranthus retroflexus, annual bluegrasses, full real each 10 in the seed that shows money or valuables one carries unintentionally of choosing is put in the culture dish, will encircle that (dried meat-phenylpropyl alcohol-) compound is made into 5,50,500mgL
-1Three concentration gradients, every ware liquid feeding 10ml respectively establishes three repetitions, places in the growth cabinet, in temperature 25, humidity 75%, cultivated 6 days under the illumination condition in 12 hours, surveys rhizome length, with clear water contrast contrast, obtains inhibiting rate, sees Fig. 2, Fig. 3.Test shows, ring (dried meat-phenylpropyl alcohol-) all has restraining effect to three kinds of plant rhizome of survey, wherein to the inhibition of root apparently higher than inhibition to stem, and different plant presents difference, wherein the inhibition to the Amaranthus retroflexus weeds obviously exceeds other two kind of plant again.
Embodiment 4: the plant growth inhibiting activity of ring (different bright-phenylpropyl alcohol-) is measured
With weeds and accelerating germination of rice seed such as Amaranthus retroflexus, annual bluegrasses, full real each 10 in the seed that shows money or valuables one carries unintentionally of choosing is put in the culture dish, will encircle that (different bright-phenylpropyl alcohol-) compound is made into 5,50,500mgL
-1Three concentration gradients, every ware liquid feeding 10ml respectively establishes three repetitions, places in the growth cabinet, in temperature 25, humidity 75%, cultivated 6 days under the illumination condition in 12 hours, surveys rhizome length, with clear water contrast contrast, obtains inhibiting rate, sees Fig. 4, Fig. 5.Test shows, ring (different bright-phenylpropyl alcohol-) all has restraining effect to three kinds of plant rhizome of survey, wherein to the inhibition of root apparently higher than inhibition to stem, but totally activity will be lower than ring (dried meat-phenylpropyl alcohol-).
Embodiment 5: the plant growth inhibiting activity of ring (Se-phenylpropyl alcohol-) is measured
With weeds and accelerating germination of rice seed such as Amaranthus retroflexus, annual bluegrasses, full real each 10 in the seed that shows money or valuables one carries unintentionally of choosing is put in the culture dish, will encircle that (Se-phenylpropyl alcohol-) compound is made into 5,50,500mgL
-1Three concentration gradients, every ware liquid feeding 10ml respectively establishes three repetitions, places in the growth cabinet, in temperature 25, humidity 75%, cultivated 6 days under the illumination condition in 12 hours, surveys rhizome length, with clear water contrast contrast, obtains inhibiting rate, sees Fig. 6, Fig. 7.Test shows, ring (Se-phenylpropyl alcohol-) all has restraining effect to three kinds of plant rhizome of survey, and wherein will be higher than inhibition to stem to the inhibition of root, different plant inhibiting rate differences, and wherein the inhibition to annual bluegrass weeds root obviously exceeds other two kind of plant.
Claims (2)
1. the biological preparation method of CYCLIC DIPEPTIDES compounds (formula 1),
cyclo-(-A
1-A
2-)
(formula 1) wherein, A
1Be Pro, Phe, Leu, a kind of aliphatic amino acid or a kind of die aromatischen Aminosaeuren;
A
2Be Try, Phe, Ile, a kind of aliphatic amino acid or a kind of die aromatischen Aminosaeuren; It is characterized in that may further comprise the steps:
1) with deposit number be: the pathogenic mutation (Xanthomonas campestris pv.retroflexus) of the high-performance bio weeding bacterium xanthomonas campestris Amaranthus retroflexus of CGMCC NO.0902 is a bacterial classification, in conventional solid medium, this bacterial classification is carried out slant culture, rejuvenation is cultivated 9-24h for 25-30 ℃; Carry out seed culture then, contain the liquid nutrient medium of 2/3 volume in the 400ml triangular flask, the prescription of liquid nutrient medium is: extractum carnis 0.5-2.2%, peptone 0.2-4%, glucose 0.2-4%, NH
4H
2PO
40.05-0.5%, NaCl0.1-2.0% supplies volume with water; Accent initial p H value is 6.0-7.4, and at the 121-125 ℃ of 20-30min that sterilizes down, the cooling back is inoculated with 1% inoculum size, cultivates 12-32h for 25-30 ℃.
2) liquid nutrient medium of Sheng 2/3 volume in the fermentor tank, the prescription of liquid nutrient medium are with the prescription of above-mentioned seed liquor body substratum, and with the inoculum size inoculation of 6-12%, air flow is 1 by volume: 0.6-1.5, cultivate 54-120h for 25-30 ℃, and get fermented liquid;
3) the centrifugal supernatant liquor that gets of fermented liquid, concentrating under reduced pressure, repeatedly precipitate the removal polysaccharide with acetone, pressure reducing and steaming acetone transfers to 3-7 with left liquid pH, with isopyknic ethyl acetate extraction for several times, combined ethyl acetate extracting solution then, its underpressure distillation is concentrated into dried, with the dissolve with methanol of 1-5 milliliter, separate with silicagel column, with sherwood oil: ethyl acetate is the gradient elution from 10: 1 to 4: 6 by volume; The part of triketohydrindene hydrate colour developing behind the hydrochloric acid hydrolysis is separated with silicagel column, component after the thin layer chromatography analysis that character is identical merges, and makes CYCLIC DIPEPTIDES compounds again.
2. the purposes of CYCLIC DIPEPTIDES compounds according to claim 1 is characterized in that this CYCLIC DIPEPTIDES compounds is used to prevent and kill off Amaranthus retroflexus, lamb's-quarters, Cassia tora, annual bluegrass and lady's-grass weeds.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009000757A1 (en) * | 2007-06-22 | 2008-12-31 | Basf Se | Piperazine compounds with herbicidal action |
| JP2009522238A (en) * | 2006-01-02 | 2009-06-11 | ビーエーエスエフ ソシエタス・ヨーロピア | Piperazine compounds with herbicidal action |
| CN101255139B (en) * | 2008-03-18 | 2012-11-07 | 沈阳药科大学 | Method for synthesizing antitumor compound of diketopiperazine PJ147 |
| CN103059031A (en) * | 2013-01-30 | 2013-04-24 | 青岛农业大学 | High-pressure reverse-phase preparation separation technology of cyclic dipeptide C7 contained in phellinus igniarius |
| CN103059032A (en) * | 2013-01-30 | 2013-04-24 | 青岛农业大学 | Separation technology of cyclic dipeptide C3 contained in phellinus igniarius |
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| CN101715770B (en) * | 2009-12-08 | 2013-10-09 | 中国科学院南海海洋研究所 | Application of loop proline-3-hydroxy-2-aminobutyric acid in preventing and removing marine fouling organisms |
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| CN1500804A (en) * | 2002-11-18 | 2004-06-02 | 清华大学 | Preparing method for thread group cyclic dipeptide |
| CN1227979C (en) * | 2003-03-19 | 2005-11-23 | 浙江大学 | High efficiency biological weed control bacterial and breeding selection method |
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| CN105441504A (en) * | 2015-11-19 | 2016-03-30 | 浙江工业大学 | Preparation method of cyclic dipeptide compound |
| CN105441504B (en) * | 2015-11-19 | 2018-10-23 | 浙江工业大学 | A kind of preparation method of CYCLIC DIPEPTIDES compounds |
| CN105859723A (en) * | 2016-04-15 | 2016-08-17 | 厦门大学 | Proline containing cyclo-dipeptide and synthesis method thereof |
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