CN116082461B - Small molecular peptide with antibacterial activity and application thereof - Google Patents
Small molecular peptide with antibacterial activity and application thereof Download PDFInfo
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- CN116082461B CN116082461B CN202211258894.5A CN202211258894A CN116082461B CN 116082461 B CN116082461 B CN 116082461B CN 202211258894 A CN202211258894 A CN 202211258894A CN 116082461 B CN116082461 B CN 116082461B
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- small molecular
- peptide
- antibacterial activity
- staphylococcus
- antibacterial
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- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 16
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 15
- 241000191940 Staphylococcus Species 0.000 claims abstract description 9
- 229940124350 antibacterial drug Drugs 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 11
- 244000063299 Bacillus subtilis Species 0.000 claims description 7
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 7
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 7
- 241000187432 Streptomyces coelicolor Species 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000022 bacteriostatic agent Substances 0.000 claims description 2
- 230000000853 biopesticidal effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000003384 small molecules Chemical class 0.000 claims 1
- 108010019477 S-adenosyl-L-methionine-dependent N-methyltransferase Proteins 0.000 abstract description 6
- 108010000785 non-ribosomal peptide synthase Proteins 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- 241000193830 Bacillus <bacterium> Species 0.000 abstract description 4
- 229930001118 polyketide hybrid Natural products 0.000 abstract description 4
- 125000003308 polyketide hybrid group Chemical group 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 241000187561 Rhodococcus erythropolis Species 0.000 abstract description 3
- 241000187747 Streptomyces Species 0.000 abstract description 3
- 238000001514 detection method Methods 0.000 abstract description 2
- 238000011161 development Methods 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 7
- 229930014626 natural product Natural products 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 235000015097 nutrients Nutrition 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 101000979117 Curvularia clavata Nonribosomal peptide synthetase Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108091008053 gene clusters Proteins 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 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 description 2
- 108090000364 Ligases Proteins 0.000 description 2
- 102000003960 Ligases Human genes 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- XZNUGFQTQHRASN-XQENGBIVSA-N apramycin Chemical compound O([C@H]1O[C@@H]2[C@H](O)[C@@H]([C@H](O[C@H]2C[C@H]1N)O[C@@H]1[C@@H]([C@@H](O)[C@H](N)[C@@H](CO)O1)O)NC)[C@@H]1[C@@H](N)C[C@@H](N)[C@H](O)[C@H]1O XZNUGFQTQHRASN-XQENGBIVSA-N 0.000 description 2
- 229950006334 apramycin Drugs 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000013028 medium composition Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000009631 Broth culture Methods 0.000 description 1
- 239000008118 PEG 6000 Substances 0.000 description 1
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 description 1
- 241000316848 Rhodococcus <scale insect> Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000000589 Siderophore Substances 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 241001655322 Streptomycetales Species 0.000 description 1
- 101150020337 TSB2 gene Proteins 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000009412 basement excavation Methods 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000012070 whole genome sequencing analysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Organic Chemistry (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Biophysics (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Genetics & Genomics (AREA)
Abstract
The invention relates to the field of pharmaceutical chemistry, and relates to a small molecular peptide with antibacterial activity and application thereof. The non-ribosomal peptide synthetase (NRPS) sequence of a strain of rhodococcus erythropolis is analyzed by bioinformatics software, the possible molecular structure of the non-ribosomal peptide synthesized by the NRPS is predicted, and a small molecular peptide is obtained by chemical synthesis, and the detection shows that the non-ribosomal peptide synthetase has better inhibition effect on the growth of streptomyces, bacillus, staphylococcus and the like, and has the development value of novel antibacterial drugs.
Description
Technical Field
The invention relates to the field of pharmaceutical chemistry, in particular to a small molecular peptide with antibacterial activity, and an inhibition effect thereof on the growth of various microorganisms and application thereof in the preparation of antibacterial drugs and biopesticides.
Background
The abuse of existing antibiotics, drug-resistant bacteria and infections caused by drug-resistant bacteria have serious consequences on a global scale, so the discovery of new antibiotics with high efficiency and high quality is an important research topic worldwide. Non-ribosomal peptides are a large family of natural products, synthesized by non-ribosomal peptide synthetases (Nonribosomal Peptide Synthetase, NRPS), many of which possess biological activities such as bacteriostatic activity, siderophore activity, etc. However, it is quite difficult to separate and purify the synthetic product from the complex fermentation product of the strain; in addition, many gene clusters are nearly silent under most culture conditions, and activation of these silent gene clusters requires extensive molecular genetic work for different strains.
With the continuous intensive research on the structure and functional relationship of natural product synthetases, bioinformatics developed some software (such as antismush, etc.) for predicting the synthetic products based on the structure of the synthetases, and researchers combined the predicted results of these software with chemical synthesis means to develop a new way of exploring natural products, namely the synthetic-natural product (syn-bioinformatic natural product, syn-BNP) method.
On the basis of carrying out whole genome sequencing on a rhodococcus erythropolis strain, the sequencing result is analyzed by using bioinformatics software, the possible molecular structure of non-ribosomal peptide synthesized by one NRPS in the genome is predicted, the small molecular peptides are obtained through chemical synthesis, and one small molecular peptide is detected to have an inhibition effect on the growth of various microorganisms.
Disclosure of Invention
In order to accelerate the excavation of natural products and enrich a natural product molecular library, the invention predicts the possible molecular structure of non-ribosomal peptide synthesized by Rhodococcus erythropolis NRPS by using software, obtains the small molecular peptides by chemical synthesis, and detects that one of the small molecular peptides has an inhibiting effect on the growth of various microorganisms.
A small molecular peptide with antibacterial activity has a chemical formula of C 29 H 46 N 6 O 6 (Compound 1) having the following structural formula:
the small molecular peptide with antibacterial activity can be applied to preparation of antibacterial drugs and biological pesticides.
The small molecular peptide has an inhibition effect on the growth of streptomyces such as streptomyces coelicolor, bacillus such as bacillus subtilis, staphylococcus epidermidis, staphylococcus pseudointermedia and the like.
The invention has the beneficial effects that: the invention obtains a small molecular peptide by digging a rhodococcus gene cluster. The antibacterial experiment shows that the compound has better inhibitory activity on streptomycete, bacillus and staphylococcus. Therefore, the compound is expected to become a lead compound of an antibacterial drug and has good development prospect.
Drawings
FIG. 1 is a positive ion mass spectrum of an antibacterial compound of the present invention
FIG. 2 is a HPLC chart of the antibacterial compound of the present invention
Detailed Description
The invention is further described with reference to the drawings and examples. Liquid nutrient broth composition used in the examples: 1% of peptone, 1% of beef extract, 0.5% of NaCl, 1% of glucose and 7.0 of pH, wherein the percentages are mass percentages. The solid nutrient broth components used in the examples were 1.5% agar (mass%) added to the liquid nutrient broth. Solid YEME medium composition used in the examples: 3 per mill of yeast powder, 5 per mill of peptone, 3 per mill of malt extract, 4 percent of glucose and 1.5 percent of agar powder. Liquid TSB medium composition used in the examples: TSB2%, PEG 6000%.
Structural analysis of (one) Compounds
The antibacterial compound is white solid, is easy to dissolve in dimethyl sulfoxide, methanol and slightly soluble in water.
ESI-MS m/e 575.3([M+H] + )。
1 H NMR(400MHz,DMSO-d6)δ8.14-7.98(m,3H),7.25-7.15(m,5H),5.01(s,1H),4.47-4.45(t,4H),4.25-4.17(m,1H),3.10(t,2H),1.83(m,5H),1.26-1.24(m,3H),1.09(d,2H),1.03(m,12H)。
(II) antibacterial Activity detection
1. Test bacteria
A pseudointermedia staphylococci; staphylococcus epidermidis; bacillus subtilis; streptomyces coelicolor
2. Determination of bacteriostatic Activity
The antibacterial activity adopts a filter paper sheet method. The staphylococcus pseudointermedia, staphylococcus epidermidis and bacillus subtilis are inoculated into a liquid nutrient broth culture medium, and the streptomyces coelicolor is inoculated into a liquid TSB culture medium for culture. Culturing to OD 600 When the bacterial liquid is 0.5, the bacterial liquid is coated on the surface of the corresponding solid culture medium (the staphylococcus pseudointermedia, the staphylococcus epidermidis and the bacillus subtilis are coated on the solid nutritionGravy medium, streptomyces coelicolor coated on solid YEME medium). Test compounds were prepared with DMSO to 20mg/mL of test solution, 8. Mu.L was pipetted with a pipette and applied to a 6mm diameter filter paper sheet, after which the DMSO was volatilized, and the medicated filter paper sheet was then applied to the medium. After culturing in an incubator of 37 ℃ (pseudo-middle staphylococcus; staphylococcus epidermidis) or 30 ℃ (bacillus subtilis; streptomyces coelicolor) for 12 hours, the diameter of the inhibition zone was measured. 10mg/ml apramycin (apramycin) was used as a positive control and DMSO was used as a negative control.
TABLE 1 antibacterial Activity of Compounds
Conclusion of experiment: the antibacterial compound has better inhibitory activity on Streptomyces coelicolor, bacillus subtilis, staphylococcus pseudointermedia and staphylococcus epidermidis. Therefore, the compound has better inhibitory activity on streptomyces, bacillus and staphylococcus. Can be directly used as a bacteriostatic agent or applied to the preparation of antibacterial drugs or biological pesticides. The invention is not limited to the specific embodiments shown, but any equivalent modifications of the technical solution of the invention will be covered by the claims of the invention by a person skilled in the art from reading the description of the invention.
Claims (3)
1. A small molecular peptide with antibacterial activity is characterized by having a chemical formula of C 29 H 46 N 6 O 6 The structural formula is as follows:
。
2. the use of a small molecule peptide according to claim 1, wherein: the compound is applied to the preparation of antibacterial drugs or biopesticides for inhibiting streptomyces coelicolor, bacillus subtilis, staphylococcus pseudointermedia or staphylococcus epidermidis.
3. A bacteriostatic agent comprising the small peptide of claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211258894.5A CN116082461B (en) | 2022-10-14 | 2022-10-14 | Small molecular peptide with antibacterial activity and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211258894.5A CN116082461B (en) | 2022-10-14 | 2022-10-14 | Small molecular peptide with antibacterial activity and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN116082461A CN116082461A (en) | 2023-05-09 |
| CN116082461B true CN116082461B (en) | 2023-11-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211258894.5A Active CN116082461B (en) | 2022-10-14 | 2022-10-14 | Small molecular peptide with antibacterial activity and application thereof |
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| Country | Link |
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| CN (1) | CN116082461B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012093855A2 (en) * | 2011-01-04 | 2012-07-12 | 한국생명공학연구원 | Novel flavi mycin compound, antifungal composition including same, and method for producing same |
| CN112321678A (en) * | 2013-10-28 | 2021-02-05 | 诺雷克斯股份有限公司 | NMDA receptor modulators and prodrugs, salts and uses thereof |
| CN113336827A (en) * | 2021-06-30 | 2021-09-03 | 中国海洋大学 | Low-molecular-weight antibacterial peptide YHX-2 and composition and application thereof |
-
2022
- 2022-10-14 CN CN202211258894.5A patent/CN116082461B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012093855A2 (en) * | 2011-01-04 | 2012-07-12 | 한국생명공학연구원 | Novel flavi mycin compound, antifungal composition including same, and method for producing same |
| CN112321678A (en) * | 2013-10-28 | 2021-02-05 | 诺雷克斯股份有限公司 | NMDA receptor modulators and prodrugs, salts and uses thereof |
| CN113336827A (en) * | 2021-06-30 | 2021-09-03 | 中国海洋大学 | Low-molecular-weight antibacterial peptide YHX-2 and composition and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 新氟喹诺酮类抗菌药普利沙星;解飞等;中国新药杂志(第9期);1198-1201 * |
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| Publication number | Publication date |
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| CN116082461A (en) | 2023-05-09 |
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