Synthetic Biology Journal ›› 2021, Vol. 2 ›› Issue (5): 674-696.DOI: 10.12211/2096-8280.2021-039
• Invited Review • Previous Articles Next Articles
Faguang ZHANG1, Ge QU2, Zhoutong SUN2, Jun′an MA1
Received:
2021-04-01
Revised:
2021-06-19
Online:
2021-11-19
Published:
2021-10-31
Contact:
Zhoutong SUN,Jun′an MA
张发光1, 曲戈2, 孙周通2, 马军安1
通讯作者:
孙周通,马军安
作者简介:
基金资助:
CLC Number:
Faguang ZHANG, Ge QU, Zhoutong SUN, Jun′an MA. From chemical synthesis to biosynthesis: trends toward total synthesis of natural products[J]. Synthetic Biology Journal, 2021, 2(5): 674-696.
张发光, 曲戈, 孙周通, 马军安. 从化学合成到生物合成——天然产物全合成新趋势[J]. 合成生物学, 2021, 2(5): 674-696.
Add to citation manager EndNote|Ris|BibTeX
URL: https://synbioj.cip.com.cn/EN/10.12211/2096-8280.2021-039
1 | BLAKEMORE P R, WHITE J D. Morphine, the proteus of organic molecules[J]. Chemical Communications, 2002, 38(11): 1159-1168. |
2 | BROOK K, BENNETT J, DESAI S P. The chemical history of Morphine: An 8000-year journey, from resin to de-novo synthesis[J]. Journal of Anesthesia History, 2017, 3(2): 50-55. |
3 | JACK D B. One hundred years of Aspirin[J]. Lancet, 1997, 350(9075): 437-439. |
4 | DESBOROUGH M J R, KEELING D M. The Aspirin story-from willow to wonder drug[J]. British Journal of Haematology, 2017, 177(5): 674-683. |
5 | 徐任生. 天然产物化学[M]. 2版. 北京: 科学出版社, 2004; |
XU R S. Natural products chemistry[M]. 2nd Ed. Beijing: Science Press, 2004. | |
6 | COOPER R. Natural products chemistry: sources, separations and structures[M]. NICOLA G, Eds. Florida: Boca Raton, 2016. |
7 | JACOB E J. Natural products-based drug discovery: some bottlenecks and considerations[J]. Current Science, 2009, 96(6): 753-754. |
8 | DAVID B, WOLFENDER J L, DIAS D A. The pharmaceutical industry and natural products: historical status and new trends[J]. Phytochemistry Reviews, 2015, 14(2): 299-315. |
9 | NEWMAN D J, CRAGG G M. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019[J]. Journal of Natural Products, 2020, 83(3): 770-803. |
10 | NICOLAOU K C, VOURLOUMIS D, WINSSINGER N, et al. The art and science of total synthesis at the dawn of the twenty-first century[J]. Angewandte Chemie International Edition, 2000, 39(1): 44-122. |
11 | NICOLAOU K C. Molecules that changed the world[M]. Weinheim: Wiley-VCH, 2008. |
12 | NICOLAOU K C. Classics in total synthesis: targets, strategies, methods[M]. Weinheim: VCH, 1996. |
13 | NICOLAOU K C. Classics in total synthesisⅡ: more targets, strategies, methods[M]. Weinheim: Wiley-VCH, 2003. |
14 | NICOLAOU K C. Classics in total synthesisⅢ: further targets, strategies, methods[M]. Weinheim: Wiley-VCH, 2011. |
15 | ROBINSON R. A synthesis of tropinone[J]. Journal of the Chemical Society, Transactions, 1917, 111: 762-768. |
16 | FISHER H, ZEILE K. Synthese des hämatoporphyrins, protoporphyrins und hämins[J]. Justus Liebigs Annalen der Chemie, 1929, 468(1): 98-116. |
17 | BACHMANN W E, COLE W, WILDS A L. The total synthesis of the sex hormone equilenin[J]. Journal of the American Chemical Society, 1939, 61(4): 974-975. |
18 | WOODWARD R B, DOERING W E. The total synthesis of quinine[J]. Journal of the American Chemical Society, 1944, 66(5): 849-850. |
19 | WOODWARD R B, SONDHEIMER F, TAUB D, et al. The total synthesis of steroids[J]. Journal of the American Chemical Society, 1952, 74(17): 4223-4251. |
20 | WOODWARD R B, SONDHEIMER F, TAUB D. The total synthesis of cortisone[J]. Journal of the American Chemical Society, 1951, 73(8): 4057. |
21 | WOODWARD R B, CAVA M P, OLLIS W D, et al. The total synthesis of strychnine[J]. Journal of the American Chemical Society, 1954, 76(18): 4749-4751. |
22 | WOODWARD R B, AYER W A, BEATON J M, et al. The total synthesis of Chlorophyll[J]. Journal of the American Chemical Society, 1960, 82(14): 3800-3802. |
23 | WOODWARD R B, HEUSLER K, GOSTELI J, et al. The total synthesis of cephalosporin C[J]. Journal of the American Chemical Society, 1966, 88(4): 852-853. |
24 | WOODWARD R B, AU-YEUNG B W, BALARAM P, et al. Asymmetric total synthesis of erythromycin. 2. Synthesis of an erythronolide A lactone system[J]. Journal of the American Chemical Society, 1981, 103(11): 3213-3215. |
25 | WOODWARD R B. Recent advances in the chemistry of natural products[J]. Pure and Applied Chemistry, 1968, 17(3): 519-547. |
26 | WOODWARD R B, HOFFMANN R. Structure of electrocyclic Reactions[J]. Journal of the American Chemical Society, 1966, 87(2): 395-397. |
27 | COREY E J, SNIDER B B. Total synthesis of (+ -)-fumagillin[J]. Journal of the American Chemical Society, 1972, 94(7): 2549-2550. |
28 | COREY E J, TRYBULSKI E J, MELVIN L S, et al. Total synthesis of erythromycins. 3. Stereoselective routes to intermediates corresponding to C(1) to C(9) and C(10) to C(13) fragments of erythronolide B[J]. Journal of the American Chemical Society, 1978, 100(14): 4618-4620. |
29 | TAMELEN E E VAN, SPENCER J T A, ALLEN J D S, et al. The total synthesis of colchicine[J]. Journal of the American Chemical Society, 1959, 81(23): 6341-6342. |
30 | COREY E J, CROUSE D N, ANDERSON J E. Total synthesis of natural 20(S)-camptothecin[J]. The Journal of Organic Chemistry, 1975, 40(14): 2140-2141. |
31 | COREY E J, SCHAAF T K, HUBER W, et al. Total synthesis of Prostaglandins F2α and E2 as the naturally occuring forms[J]. Journal of the American Chemical Society, 1970, 92(2): 397-398. |
32 | FUKUYAMA T, YANG L H, AJECK K L, et al. Total synthesis of (.+ -.)-saframycin A[J]. Journal of the American Chemical Society, 1990, 112(9): 3712-3713. |
33 | COREY E J, HUA D H, PAN B C, et al. Total synthesis of aplasmomycin[J]. Journal of the American Chemical Society, 1982, 104(24): 6818-6820. |
34 | COREY E J, CHENG X M. The logic of chemical synthesis[M]. New York: Wiley, 1989. |
35 | KUNG Y T, DU Y C, HUANG W T, et al. Total synthesis of crystalline bovine insulin[J]. Scientia Sinica, 1965, 14(11): 1710-1716. |
36 | KUNG Y T, DU Y C, HUANG W D, et al. Total synthesis of crystalline insulin[J]. Scientia Sinica, 1966, 15(4): 544-561. |
37 | MCELHENY V K. Total synthesis of insulin in red China[J]. Science, 1966, 153(3733): 281-283. |
38 | 中国科学院上海生物化学研究所, 等. 酵母丙氨酸转移核糖核酸的全合成[J]. 科学通报, 1982, 27(2): 106-109. |
Shanghai Institute of Biochemistry and Cell Biology, Chinese Academy of Sciences, et al. The total synthesis of yeast alanine transfer RNA[J]. Chinese Science Bulletin, 1982, 27(2): 106-109. | |
39 | 王德宝, 郑可沁, 裘慕绥, 等. 酵母丙氨酸转移核糖核酸(酵母丙氨酸t-RNA)人工全合成[J]. 中国科学: B辑, 1983, 26(5): 385-398. |
WANG D B, ZHENG, K Q, QIU M S, et al. The man-total synthesis of yeast alanine transfer RNA[J]. Scientia Sinica: B, 1983, 26(5): 385-398. | |
40 | 许杏祥, 朱杰, 黄大中, 等. 青蒿素及其一类物结构和合成的研究X: 从青蒿酸立体控制合成青蒿素和脱氧青蒿素[J]. 化学学报, 1983, 41(6): 574-576. |
XU X X, ZHU J, HUANG D Z, et al. Studies on structure and syntheses of arteannuin and related compound XVII: The stereocontrolled synthesis of arteannuin and deoxyarteannuin from arteannuic acid[J]. Acta Chimica Sinica, 1983, 41(6): 574-576. | |
41 | 许杏祥, 朱杰, 黄大中, 等. 青蒿素及其一类物结构和合成的研究ⅩⅦ: 双氢青蒿酸甲酯的立体控制性全合成——青蒿素全合成[J]. 化学学报, 1984, 42(9): 940-942. |
XU X X, ZHU J, HUANG D Z, et al. Studies on structure and syntheses of arteannuin and related compound ⅩⅦ: The stereocontrolled total synthesis of methyl dihydroarteannuate─the total synthesis of arteannuin[J]. Acta Chimica Sinica, 1984, 42(9): 940-942. | |
42 | NICOLAOU K C, YANG Z, LIU J J, et al. Total synthesis of taxol[J]. Nature, 1994, 367(6464): 630-634. |
43 | HOLTON R A, SOMOZA C, KIM H B, et al. First total synthesis of taxol: 1. Functionalization of the B ring[J]. Journal of the American Chemical Society, 1994, 116(4): 1597-1598. |
44 | HOLTON R A, KIM H B, SOMOZA C, et al. First total synthesis of taxol: 2. Completion of the C and D rings[J]. Journal of the American Chemical Society, 1994, 116(4): 1599-1600. |
45 | CHAUVIÉRE G, GUÉNARD D, PICOT F, et al. Structure and biochemistry of products isolated from Taxus baccata[J]. Seances de l'Academie des Sciences—SerieⅡ, 1981, 293(7): 501-503. |
46 | J-N DENIS, GREENE A E, GUENARD D, et al. Highly efficient, practical approach to natural taxol[J]. Journal of the American Chemical Society, 1988, 110(17): 5917-5919. |
47 | GUENARD D, GUERITTE-VOEGELEIN F, POTIER P. Taxol and taxotere: discovery, chemistry, and structure-activity relationships[J]. Accounts of Chemical Research, 1993, 26(4): 160-167. |
48 | BALOGLU E, KINGSTON D G I. A new semisynthesis of paclitaxel from baccatinⅢ[J]. Journal of Natural Products, 1999, 62(7): 1068-1071. |
49 | NICOLAOU K C, MITCHELL H J, JAIN N F, et al. Total synthesis of vancomycin[J]. Angewandte Chemie International Edition, 1999, 38(1): 240-244. |
50 | EVANS D A, WOOD M R, TROTTER B W, et al. Total syntheses of vancomycin and eremomycin aglycons[J]. Angewandte Chemie International Edition, 1998, 37(19): 2700-2704. |
51 | BOGER D L, MIYAZAKI S, KIM S H, et al. Total synthesis of the vancomycin aglycon[J]. Journal of the American Chemical Society, 1999, 121(43): 10004-10011. |
52 | MADDESS M L, TACKETT M N, WATANABE H, et al. Total synthesis of rapamycin[J]. Angewandte Chemie International Edition, 2007, 46(4): 591-597. |
53 | SUH E M, KISHI Y. Synthesis of palytoxin from palytoxin carboxylic acid[J]. Journal of the American Chemical Society, 1994, 116(24): 11205-11206. |
54 | KISHI Y, ARATANI M, FUKAYAMA T, et al. Synthetic studies on tetrodotoxin and related compounds.Ⅲ. Stereospecific synthesis of an equivalent of acetylated tetrodamine[J]. Journal of the American Chemical Society, 1972, 94(26): 9217-9219. |
55 | AICHER T D, BUSZEK K R, FANG F G, et al. Total synthesis of halichondrin B and norhalichondrin B[J]. Journal of the American Chemical Society, 1992, 114(8): 3162-3164. |
56 | ZHENG W J, SELETSKY B M, PALME M H, et al. Macrocyclic ketone analogues of halichondrin B[J]. Bioorganic & Medicinal Chemistry Letter, 2004, 14(22): 5551-5554. |
57 | YU M J, ZHENG W J, SELETSKY B M, et al. Case history: discovery of eribulin (HALAVEN (TM)), a halichondrin B analogue that prolongs overall survival in patients with metastatic breast cancer[J]. Annual Reports in Medicinal Chemistry, 2011, 46: 227-241. |
58 | YU M J, ZHENG W J, SELETSKY M B. From micrograms to grams: scale-up synthesis of eribulin mesylate[J]. Natural Product Report, 2013, 30(9): 1158-1164. |
59 | 卢志国, 汪建峰, 蒙海林, 等. 合成生物学与天然产物开发[J]. 生命科学, 2011, 23(9): 900-911. |
LU Z G, WANG J F, MENG H L, et al. Synthetic biology and natural products development[J]. Chinese Bulletin of Life Sciences, 2011, 23(9): 900-911. | |
60 | 潘海学, 袁华, 蹇晓红, 等. 天然产物生物合成与抗肿瘤药物合成生物学研究[J]. 中国科学:生命科学, 2015, 45(10): 1027-1039. |
PAN H X, YUAN H, JIAN X H, et al. Biosynthesis of natural products and synthetic biology of antitumor drugs[J]. Scientia Sinica Vitae, 2015, 45(10): 1027-1039. | |
61 | SHELDON R A,WOODLEY J M. Role of biocatalysis in sustainable chemistry[J]. Chemical Reviews, 2018, 118(2): 801-838. |
62 | 贺俊斌, 孟松, 潘海学, 等. 多酶催化串联策略在复杂天然产物合成中的应用[J]. 合成生物学, 2020, 1(2): 226-246. |
HE J B, MENG S, PAN H X, et al. Applications of the multienzyme-catalyzed tandem strategy in the synthesis of complex natural products[J]. Synthetic Biology Journal, 2020, 1(2): 226-246. | |
63 | CURRIN A, SWAINSTON N, DAY P J, et al. Synthetic biology for the directed evolution of protein biocatalysts: navigating sequence space intelligently[J]. Chemical Society Reviews, 2015, 44(5): 1172-1239. |
64 | CRAVENS A, PAYNE J, SMOLKE C D. Synthetic biology strategies for microbial biosynthesis of plant natural products[J]. Nature Communications, 2019, 10(1): 2142. |
65 | 饶聪, 云轩, 虞沂, 等. 微生物药物的合成生物学研究进展[J]. 合成生物学, 2020, 1(1): 92-102. |
RAO C, YUN X, YU Y, et al. Recent progress of synthetic biology applications in microbial pharmaceuticals research[J]. Synthetic Biology Journal, 2020, 1(1): 92-102. | |
66 | PALAZZOTTO E, TONG Y, LEE S Y, et al. Synthetic biology and metabolic engineering of actinomycetes for natural product discovery[J]. Biotechnology Advances, 2019, 37(6): 107366. |
67 | HODGKIN D C. The X-ray analysis of the structure of penicillin[J]. Advancement of Science, 1949, 6(22): 85-89. |
68 | MARTÍN J F, DÍEZ B, ALVAREZ E, et al. Development of a transformation system in Penicillium chrysogenum: cloning of genes involved in penicillin biosynthesis[M]//ALACEVIC M, HRANUELI D, TOMAN Z. Genetics of industrial microorganism. Zagreb: Pliva, 1987: 297-308. |
69 | ALVAREZ E, CANTORAL J M, BARREDO J L, et al. Purification to homogeneity and characterization of acyl coenzyme A: 6-aminopenicillanic acid acyltransferase of Penicillium chrysogenum[J]. Antimicrob Agents Chemother, 1987, 31(11): 1675-1682. |
70 | MCGUIRE J M, BUNCH R L, ANDERSON R C, et al. Ilotycin, a new antibiotic[J]. Antibiotics and Chemotherapy, 1952, 2(6): 281-283. |
71 | CHEN L, SUN S F, SONG G W. Biosynthesis and combinatorial biosynthesis of erythromycin[J]. Chinese Journal of Organic Chemistry, 2012, 32(7): 1232-1240. |
72 | 陈单丹, 吴杰群, 刘文. 以生物合成为基础的红霉素A的产量提高和结构改造[J]. 生物工程学报, 2015, 31(6): 939-954. |
CHEN D D, WU J Q, LIU W. Biosynthesis-based production improvement and structure modification of erythromycin A[J]. Chinese Journal of Biotechnology, 2015, 31(6): 939-954. | |
73 | CHEN Y, DENG W, WU J Q, et al. Genetic modulation of the overexpression of tailoring genes eryK and eryG leading to the improvement of erythromycin a purity and production in Saccharopolyspora erythraea fermentation[J]. Applied Environmental Microbiology, 2008, 74(6): 1820-1828. |
74 | CAMPBELL W C. History of avermectin and ivermectin, with notes on the history of other macrocyclic lactone antiparasitic agents[J]. Current Pharmaceutical Biotechnology2012, 13(6): 853-865. |
75 | IKEDA H, NONOMIYA T, USAMI M, et al. Organization of the biosynthetic gene cluster for the polyketide anthelmintic macrolide avermectin in Streptomyces avermitilis[J]. Proceedings of the National Academy of Sciences of the United States of America, 1999, 96(17): 9509-9514. |
76 | OMURA S, IKEDA H, ISHIKAWA J, et al. Genome sequence of an industrial microorganism Streptomyces avermitilis: deducing the ability of producing secondary metabolites[J]. Proceedings of the National Academy of Sciences of the United States of America, 2001, 98(21): 12215-12220. |
77 | YOON Y J, KIM E S, HWANG Y S, et al. Avermectin: biochemical and molecular basis of its biosynthesis and regulation[J]. Applied Microbiology and Biotechnology, 2004, 63(6): 626-634. |
78 | ZHUO Y, ZHANG W Q, CHEN D F, et al. Reverse biological engineering of hrdB to enhance the production of avermectins in an industrial strain of Streptomyces avermitilis[J]. Proceedings of the National Academy of Sciences of the United States of America, 2010, 107(25): 11250-11254. |
79 | LIU W S, STEWART C N. Plant synthetic biology[J]. Trends in Plant Science, 2015, 20(5): 309-317. |
80 | POUVREAU B, VANHERCKE T, SINGH S. From plant metabolic engineering to plant synthetic biology: the evolution of the design/build/test/learn cycle[J]. Plant Science, 2018, 273: 3-12. |
81 | 张博, 马永硕, 尚轶, 等. 植物合成生物学研究进展[J]. 合成生物学, 2020, 1(2): 121-140. |
ZHANG B, MA Y S, SHANG Y, et al. Recent advances in plant synthetic biology[J]. Synthetic Biology Journal, 2020, 1(2): 121-140. | |
82 | WOODWARD R B. The total synthesis of vitamin B12[J]. Pure and Applied Chemistry, 1973, 33(1): 145-178. |
83 | ESCHENMOSER A, WINTNER C. Natural product synthesis and vitamin B12[J]. Science, 1977, 196(4297): 1410-1420. |
84 | FANG H, LI D, KANG J, et al. Metabolic engineering of Escherichia coli for de novo biosynthesis of vitamin B12[J]. Nature Communications, 2018, 9(1): 4917. |
85 | HUANG J P,WANG Y J,TIAN T,et al. Tropane alkaloid biosynthesis: a centennial review[J]. Natural Product Reports, 2021, 38(9): 1634-1658 |
86 | QIU F, YANG C X, YUAN L N, et al. A phenylpyruvic acid reductase is required for biosynthesis of tropane alkaloids[J]. Organic Letters, 2018, 20(24): 7807-7810. |
87 | QIU F, ZENG J L, WANG J, et al. Functional genomics analysis reveals two novel genes required for littorine biosynthesis[J]. The New Phytologist, 2020, 225(5): 1906-1914. |
88 | ZHAO T, LI S, WANG J, et al. Engineering tropane alkaloid production based on metabolic characterization of ornithine decarboxylase in Atropa belladonna[J]. ACS Synthetic Biology, 2020, 9(2): 437-448. |
89 | HUANG J P, FANG C, MA X, et al. Tropane alkaloids biosynthesis involves an unusual typeⅢ polyketide synthase and non-enzymatic condensation[J]. Nature Communications, 2019, 10: 4036. |
90 | QIU F, YAN Y J, ZENG J L, et al. Biochemical and metabolic insights into hyoscyamine dehydrogenase[J]. ACS Catalysis, 2021, 11(5): 2912-2924. |
91 | SRINIVASAN P, SMOLKE C D. Biosynthesis of medicinal tropane alkaloids in yeast[J]. Nature, 2020, 585(7826): 614-619. |
92 | LI J, AMATUNI A, RENATA H. Recent advances in the chemoenzymatic synthesis of bioactive natural products[J]. Current Opinion in Chemical Biology, 2020, 55: 111-118. |
93 | 李晓军, 张万斌, 高栓虎. 复杂天然产物全合成: 化学合成与生物合成结合的策略[J]. 有机化学, 2018, 38: 2185-2198. |
LI X J, ZHANG W B, GAO S H. Total synthesis of complex natural products: combination of chemical synthesis and biosynthesis strategies[J]. Chinese Journal of Organic Chemistry, 2018, 38: 2185-2198. | |
94 | ITAKURA K, HIROSE T, CREA R, et al. Expression in Escherichia coli of a chemically synthesized gene for the hormone somatostatin[J]. Science, 1977, 198(4321): 1056-1063. |
95 | CREA R, KRASZEWSKI A, HIROSE T, et al. Chemical synthesis of genes for human insulin[J]. Proceedings of the National Academy of Sciences of the United States of America, 1978, 75(12): 5765-5769. |
96 | GOEDEEL D V, KLEID D G, BOLIVAR F, et al. Expression in Escherichia coli of chemically synthesized genes for human insulin[J]. Proceedings of the National Academy of Sciences of the United States of America, 1979, 76(1): 106-110. |
97 | RIGGS A D. Making, cloning, and the expression of human insulin genes in bacteria: the path to humulin[J]. Endocrine Reviews, 2021, 42(3): 374-380. |
98 | 屠呦呦. 青蒿及青蒿素类药物[M]. 北京: 化学工业出版社, 2015. |
TU Y Y. Relative drugs of qinghao and qinghaosu[M]. Beijing: Chemical Industrial Press, 2015. | |
99 | PADDON C J, WESTFALL P J, PITERA D J, et al. High-level semi-synthetic production of the potent antimalarial artemisinin[J]. Nature, 2013, 496(7446): 528-532. |
100 | TURCONI J, GRIOLET F, GUEVEL R, et al. Semisynthetic artemisinin, the chemical path to industrial production[J]. Organic Process Research & Development, 2014, 18(3): 417-422. |
101 | AMARA Z, BELLAMY J F B, HORVATH R, et al. Applying green chemistry to the photochemical route to artemisinin[J]. Nature Chemistry, 2015, 7(6): 489-495. |
102 | SCOTT J D, WILLIAMS R M, Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics[J]. Chemical Reviews, 2002, 102:1669-1730. |
103 | CHRZANOWSKA M, GRAJEWSKA A, ROZWADOWSKA M D. Asymmetric synthesis of isoquinoline alkaloids: 2004-2015[J]. Chemical Reviews, 2016, 116(19): 12369-12465. |
104 | GLENN W S, RUNGUPHAN W, O'CONNO S E. Recent progress in the metabolic engineering of alkaloids in plant systems [J]. Current Opinion in Chemical Biology, 2013, 24:354-365. |
105 | TANIFUJI R, KOKETSU K, TAKAKURA M, et al. Chemo-enzymatic total syntheses of jorunnamycin A, saframycin A, and N‑Fmoc saframycin Y3[J]. Journal of the American Chemical Society, 2018, 140:10705-10709. |
106 | PYSER J B, DOCKREY S A B, BENITEZ A R, et al. Stereodivergent, chemoenzymatic synthesis of azaphilone natural products[J]. Journal of the American Chemical Society, 2019, 141(46): 18551-18559. |
107 | CHAKRABARTY S, ROMERO E O, PYSER J B, et al. Chemoenzymatic total synthesis of natural products[J]. Accounts of Chemical Research, 2021, 54(6): 1374-1384. |
108 | WERNER P, VOIGT M, KEINÄNEN K, et al. Cloning of a putative high-affinity kainate receptor expressed predominantly in hippocampal CA3 cells[J]. Nature, 1991, 351: 742-744. |
109 | STATHAKIS C I, YIOTI E G, GALLOS J K, Total Syntheses of (-)‐α‐kainic acid[J]. European Journal of Organic Chemistry, 2012: 4661-4673. |
110 | CHEKAN J R, MCKINNIE S M K, MOORE M L, et al. Scalable biosynthesis of the seaweed neurochemical, kainic acid[J]. Angewandte Chemie International Edition, 2019, 58: 8454-8457. |
111 | SHAH Z, GOHAR U F, JAMSHED I, et al. Podophyllotoxin: history, recent advances and future prospects[J]. Biomolecules, 2021, 11: 603-629. |
112 | CHANG W C, YANG Z J, TU Y H, et al. Reaction mechanism of a nonheme iron enzyme catalyzed oxidative cyclization via C-C bond formation[J]. Organic Letters, 2019, 21(1): 228-232. |
113 | LAZZAROTTO M, HAMMERER L, HETMANN M, et al. Chemoenzymatic total synthesis of deoxy-, epi-, and podophyllotoxin and a biocatalytic kinetic resolution of dibenzylbutyrolactones[J]. Angewandte Chemie International Edition, 2019, 58: 8226-8230. |
114 | LI J, ZHANG X, RENATA H. Asymmetric chemoenzymatic synthesis of ((-))-podophyllotoxin and related aryltetralin lignans[J]. Angewandte Chemie International Edition, 2019, 58(34): 11657-11660. |
115 | DAI Z B, WANG B B, LIU Y, et al. Producing aglycons of ginsenosides in bakers' yeast[J]. Scientific Reports, 2014, 4: 3698. |
116 | 王高丽, 金雪芮, 罗云孜. 合成生物学在含氟化合物生产中的应用[J]. 合成生物学, 2020, 1(3): 358-371. |
WANG G L, JIN X R, LUO Y Z. Applications of synthetic biology in the production of fluorinated compounds[J]. Synthetic Biology Journal, 2020, 1(3): 358-371. | |
117 | O' HAGAN D, SCHAFFRATH C, COBB S L, et al. Biochemistry: biosynthesis of an organofluorine molecule[J]. Nature, 2002, 416(6878): 279. |
118 | THURONYI B W, CHANG M C Y. Synthetic biology approaches to fluorinated polyketides[J]. Accounts of Chemical Research, 2015, 48(3): 584-592. |
119 | NIE J, GUO H C, CAHARD D, et al. Asymmetric construction of stereogenic carbon centers featuring a trifluoromethyl group from prochiral trifluoromethylated substrates[J]. Chemical Reviews, 2011, 111(2): 455-529. |
120 | MA J A, CAHARD D. Update 1 of: asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions[J]. Chemical Reviews, 2008, 108(9): PR1-PR43. |
121 | HUANG Q L, ROESSNER C A, CROTEAU R, et al. Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol[J]. Bioorganic & Medicinal Chemistry, 2001, 9(9): 2237-2242. |
122 | LI J H, DAI J G, CHEN X G, et al. Microbial transformation of cephalomannine by Luteibacter sp[J]. Journal of Natural Products, 2007, 70(12): 1846-1849. |
123 | AJIKUMAR P K, XIAO W H, TYO K E J, et al. Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli[J]. Science, 2010, 330(6000): 70-74. |
124 | MALIK S, CUSIDO R M, MIRJALILI M H, et al. Production of the anticancer drug taxol in Taxus Baccata suspension cultures: a review[J]. Process Biochemistry, 2011, 46(1): 23-34. |
125 | HOWAT S, PARK B, OH I S, et al. Paclitaxel: biosynthesis, production and future prospects[J]. New Biotechnology, 2014, 31(3): 242-245. |
126 | MUCHIRI R, WALKER K D. Paclitaxel biosynthesis: adenylation and thiolation domains of an NRPS TycA PheAT module produce various arylisoserine CoA thioesters[J]. Biochemistry, 2017, 56(10): 1415-1425. |
127 | FARHADI S, MOIENI A, SAFAIE N, et al. Fungal cell wall and methyl-β-cyclodextrin synergistically enhance paclitaxel biosynthesis and secretion in Corylus avellana cell suspension culture[J]. Scientific Reports, 2020, 10: 5427. |
128 | 蒋迎迎, 曲戈, 孙周通. 机器学习助力酶定向进化[J]. 生物学杂志, 2020, 37(4): 1-11. |
JIANG Y Y, QU G, SUN Z T. Machine learning-assisted enzyme directed evolution[J]. Journal of Biology, 2020, 37(4): 1-11. | |
129 | LI G Y, DONG Y J, REETZ M T. Can machine learning revolutionize directed evolution of selective enzymes?[J]. Advanced Synthesis & Catalysis, 2019, 361(11): 2377-2386. |
130 | BASTANLARY, OZUYSAL M. Introduction to machine learning[M]. Methods in Molecular Biology, 2014: 105-128. |
[1] | Zhidian DIAO, Xixian WANG, Qing SUN, Jian XU, Bo MA. Advances and applications of single-cell Raman spectroscopy testing and sorting equipment [J]. Synthetic Biology Journal, 2023, 4(5): 1020-1035. |
[2] | Hui LU, Fangli ZHANG, Lei HUANG. Establishment of iBioFoundry for synthetic biology applications [J]. Synthetic Biology Journal, 2023, 4(5): 877-891. |
[3] | Zhonghu BAI, He REN, Jianqi NIE, Yang SUN. The recent progresses and applications of in-parallel fermentation technology [J]. Synthetic Biology Journal, 2023, 4(5): 904-915. |
[4] | Yujie WU, Xinxin LIU, Jianhui LIU, Kaiguang Yang, Zhigang SUI, Lihua ZHANG, Yukui ZHANG. Research progress of strain screening and quantitative analysis of key molecules based on high-throughput liquid chromatography and mass spectrometry [J]. Synthetic Biology Journal, 2023, 4(5): 1000-1019. |
[5] | Zhehui HU, Juan XU, Guangkai BIAN. Application of automated high-throughput technology in natural product biosynthesis [J]. Synthetic Biology Journal, 2023, 4(5): 932-946. |
[6] | Huan LIU, Qiu CUI. Advances and applications of ambient ionization mass spectrometry in screening of microbial strains [J]. Synthetic Biology Journal, 2023, 4(5): 980-999. |
[7] | Yannan WANG, Yuhui SUN. Base editing technology and its application in microbial synthetic biology [J]. Synthetic Biology Journal, 2023, 4(4): 720-737. |
[8] | Wanqiu LIU, Xiangyang JI, Huiling XU, Yicong LU, Jian LI. Cell-free protein synthesis system enables rapid and efficient biosynthesis of restriction endonucleases [J]. Synthetic Biology Journal, 2023, 4(4): 840-851. |
[9] | Meili SUN, Kaifeng WANG, Ran LU, Xiaojun JI. Rewiring and application of Yarrowia lipolytica chassis cell [J]. Synthetic Biology Journal, 2023, 4(4): 779-807. |
[10] | Fanzhong ZHANG, Changjun XIANG, Lihan ZHANG. Advances and applications of evolutionary analysis and big-data guided bioinformatics in natural product research [J]. Synthetic Biology Journal, 2023, 4(4): 629-650. |
[11] | Zhi SUN, Ning YANG, Chunbo LOU, Chao TANG, Xiaojing YANG. Rational design for functional topology and its applications in synthetic biology [J]. Synthetic Biology Journal, 2023, 4(3): 444-463. |
[12] | Qilong LAI, Shuai YAO, Yuguo ZHA, Hong BAI, Kang NING. Microbiome-based biosynthetic gene cluster data mining techniques and application potentials [J]. Synthetic Biology Journal, 2023, 4(3): 611-627. |
[13] | Qiaozhen MENG, Fei GUO. Applications of foldability in intelligent enzyme engineering and design: take AlphaFold2 for example [J]. Synthetic Biology Journal, 2023, 4(3): 571-589. |
[14] | Sheng WANG, Zechen WANG, Weihua CHEN, Ke CHEN, Xiangda PENG, Fafen OU, Liangzhen ZHENG, Jinyuan SUN, Tao SHEN, Guoping ZHAO. Design of synthetic biology components based on artificial intelligence and computational biology [J]. Synthetic Biology Journal, 2023, 4(3): 422-443. |
[15] | Hailong LV, Jian WANG, Hao LV, Jin WANG, Yong XU, Dayong GU. Synthetic biology for next-generation genetic diagnostics [J]. Synthetic Biology Journal, 2023, 4(2): 318-332. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||