Error Correction Techniques in Synthetic Oligonucleotides and Synthetic DNA

Michelson A., Todd A. 1955. Nucleotides part XXXII. Synthesis of a dithymidine dinucleotide containing a 3′: 5′-internucleotidic linkage. J. Chem. Soc. 2632‒2638.

Gilham P.T., Khorana H.G. 1958. Studies on polynucleotides. I. A new and general method for the chemical synthesis of the C5″–C3″ internucleotidic linkage. Syntheses of deoxyribo-dinucleotides. J. Am. Chem. Soc. 80 (23), 6212‒6222.

CAS  Google Scholar 

Reese C.B. 2005. Oligo- and poly-nucleotides: 50 years of chemical synthesis. Org. Biomol. Chem. 3 (21), 3851–3868.

CAS  PubMed  Google Scholar 

Sinyakov A.N., Ryabinin V.A., Kostina E.V. 2021. Application of array-based oligonucleotides for synthesis of genetic designs. Mol. Biol. (Moscow). 55 (4), 487–500.  https://doi.org/10.1134/S0026893321030109

CAS  Google Scholar 

Agarwal K.L., Büchi H., Caruthers M.H., Gupta N., Khorana H.G., Kleppe K., Kumar A., Ohtsuka E., Rajbhandary U.L., Van de Sande J.H., Sgaramella V., Weber H., Yamada T. 1970. Total synthesis of the gene for an alanine transfer ribonucleic acid from yeast. Nature. 227, 27–34.

CAS  PubMed  Google Scholar 

Sekiya T., Takeya T., Brown E.L., Belagaje R., Contreras R., Fritz H.J., Gait M.J., Lees R.G., Ryan M.J., Khorana H.G., Norris K.E. 1979. Total synthesis of a tyrosine suppressor transfer RNA gene. XVI. Enzymatic joinings to form the total 207-base pair-long DNA. J. Biol. Chem. 254, 5787–5801.

CAS  PubMed  Google Scholar 

Cello J., Paul A.V., Wimmer E. 2002. Chemical synthesis of poliovirus cDNA: Generation of infectious virus in the absence of natural template. Science. 297, 1016–1018.

CAS  PubMed  Google Scholar 

Smith H.O., Hutchison C.A.III, Pfannkoch C., Venter J.C. 2003. Generating a synthetic genome by whole genome assembly: φX174 bacteriophage from synthetic oligonucleotides. Proc. Natl. Acad. Sci. U. S. A. 100 (26), 15440–15445.

CAS  PubMed  PubMed Central  Google Scholar 

Noyce R.S., Lederman S., Evans D.H. 2018. Construction of an infectious horsepox virus vaccine from chemically synthesized DNA fragments. PLoS One. 19 (13), e0188453.

Google Scholar 

Gibson D.G., Benders G.A., Andrews-Pfannkoch C., Denisova E.A., Baden-Tillson H., Zaveri J., Stockwell T.B., Brownley A., Thomas D.W., Algire M.A., Merryman C., Young L., Noskov V.N., Glass J.I., Venter J.C. Hutchison C.A. 3rd, Smith H.O. 2008. Complete chemical synthesis, assembly, and cloning of a Mycoplasma genitalium genome. Science. 319, 1215–1220.

CAS  PubMed  Google Scholar 

Gibson D.G., Glass J.I., Lartigue C., Noskov V.N., Chuang R.Y., Algire M.A., Benders G.A., Montague M.G., Ma L., Moodie M.M., Merryman C, Vashee S., Krishnakumar R., Assad-Garcia N., Andrews-Pfannkoch C., Hutchison C.A., 3rd, Smith H.O. 2010. Creation of a bacterial cell controlled by a chemically synthesized genome. Science. 329, 52–56.

CAS  PubMed  Google Scholar 

Venetz J.E., Medico L.D., Wölfle A., Schächle P., Bucher Y., Appert D., Tschan F., Flores-Tinoco C.E., van Kooten M., Guennoun R., Deutsch S., Christen M., Christen B. 2019. Chemical synthesis rewriting of a bacterial genome to achieve design flexibility and biological functionality. Proc. Natl. Acad. Sci. U. S. A. 116 (16), 8070–8079.

CAS  PubMed  PubMed Central  Google Scholar 

Filges S., Mouhanna P., Ståhlberg A. 2021. Digital quantification of chemical oligonucleotide synthesis errors. Clin. Chem. 67 (10), 1384–1394.

PubMed  Google Scholar 

Caruthers M. 1985. Gene synthesis machines: DNA chemistry and its uses. Science. 230 (4723), 281–285.

CAS  PubMed  Google Scholar 

Eckstein F. 1991. Oligonucleotides and analogues: a practical approach. IRL Press.

Google Scholar 

Ellington A., Pollard J.D.Jr. 2001. Introduction to the synthesis and purification of oligonucleotides. Curr. Protoc. Nucleic Acid Chem. Appendix 3C.

Jensen M.A., Davis R.W. 2018. Template-independent enzymatic oligonucleotide synthesis (TiEOS): Its history, prospects, and challenges. Biochemistry. 57 (12), 1821–1832.

CAS  PubMed  Google Scholar 

Pichon M., Hollenstein M. 2024. Controlled enzymatic synthesis of oligonucleotides. Commun. Chem. 7, 138.

CAS  PubMed  PubMed Central  Google Scholar 

Verardo D., Adelizzi B., Rodriguez-Pinzon D.A., Moghaddam N., Thomée E., Loman T., Godron X., Horgan A. 2023. Multiplex enzymatic synthesis of DNA with single-base resolution. Sci. Adv. 9 (27), eadi0263.

Eisenstein M. 2020. Enzymatic DNA synthesis enters new phase. Nat. Biotechnol. 38, 1113–1115.

CAS  PubMed  Google Scholar 

Amazon Prime for DNA—Has A New Era of Oligonucleotide Synthesis Begun? Oligonucleotide Therapeutics Society. https://www.oligotherapeutics.org/amazon-prime-for-dna-has-a-new-era-of-oligonucleotide-synthesis-begun/.

Ma S., Saaem I., Tian J. 2012. Error correction in gene synthesis technology. Trends Biotechnol. 30 (3), 147–154.

CAS  PubMed  Google Scholar 

Sinha N.D., Jung K.E. 2015. Analysis and purification of synthetic nucleic acids using HPLC. Curr. Protoc. Nucleic Acid Chem. 61, 10.5.1–10.5.39.

Fang S.Y., Fueangfung S. 2010. Scalable synthetic oligodeoxynucleotide purification with use of a catching by polymerization, washing, and releasing approach. Org. Lett. 12, 3720−3723.

CAS  PubMed  Google Scholar 

Pokharel D., Fang S. 2014. A highly convenient procedure for oligodeoxynucleotide purification. Open Org. Chem. J. 8, 15–18.

CAS  Google Scholar 

Fang S., Arneson R., Yin Y., Yuan Y. 2024. De novo synthesis of error-free long oligos. Curr. Protoc. 4 (10), e70028.

PubMed  Google Scholar 

Pokharel D., Fang S.Y. 2016. Polymerizable phosphoramidites with an acid-cleavable linker for eco-friendly synthetic oligodeoxynucleotide purification. Green Chem. 18, 1125–1136.

CAS  Google Scholar 

Eriyagama D., Shahsavari S., Halami B., Lu B.Y., Wei F., Fang S. 2018. Parallel, large-scale, and long synthetic oligodeoxynucleotide purification using the catching full-length sequence by polymerization technique. Org. Process Res. Dev. 22, 1282‒1288.

CAS  PubMed  PubMed Central  Google Scholar 

Jensen M., Davis R. 2017. RecJ 5′ exonuclease digestion of oligonucleotide failure strands: A “Green” method of Trityl-On purification. Biochemistry. 56 (18), 2417–2424.

CAS  PubMed  Google Scholar 

Lietard J., Leger A., Erlich Y., Sadowski N., Timp W., Somoza M.M. 2021. Chemical and photochemical error rates in light-directed synthesis of complex DNA libraries. Nucleic Acids Res. 49 (12), 6687−6701.

CAS  PubMed  PubMed Central  Google Scholar 

Zhou X., Cai S., Hong A., You Q., Yu P., Sheng N., Srivannavit O., Muranjan S., Rouillard J.M., Xia Y., Zhang X., Xiang Q., Ganesh R., Zhu Q., Matejko A., Gulari E., Gao X. 2004. Microfluidic PicoArray synthesis of oligodeoxynucleotides and simultaneous assembling of multiple DNA sequences. Nucleic Acids Res. 32, 5409–5417.

CAS  PubMed  PubMed Central  Google Scholar 

Tian J., Gong H., Sheng N., Zhou X., Gulari E., Gao X., Church G. 2004. Accurate multiplex gene synthesis from programmable DNA microchips. Nature. 432, 1050–1054.

CAS  PubMed  Google Scholar 

Church G.M., Tian J. 2005. WO Patent No. 2005/089110 A2. Geneva: Switzerland World Intellectual Property Organization International Bureau.

Church G.M., Tian J. 2006. US Patent No. 2006/0127920 A1. Washington, DC: U.S. Patent and Trademark Office.

Borovkov A.Y., Loskutov A.V., Robida M.D., Day K.M., Cano J.A., Olson T.L., Patel H., Brown K., Hunter P.D., Sykes K.F. 2010. High-quality gene assembly directly from unpurified mixtures of microarray-synthesized oligonucleotides. Nucleic Acids Res. 38 (19), e180.

PubMed  PubMed Central  Google Scholar 

Sun H.H., Zhu C., Wu Y., Guo J.-F. 2009. De novo synthesis and assembly of multiplex riboswitches in vitro. Biotechnol. Prog. 25 (5), 1228–1235.

CAS  PubMed  Google Scholar 

Hsiau T.H.-C., Sukovich D., Elms P., Prince R.N., Stritmatter T., Ruan P., Curry B., Anderson P., Sampson J., Anderson J.C. 2015. A method for multiplex gene synthesis employing error correction based on expression. PLoS One. 10 (3), e0119927.

PubMed  PubMed Central  Google Scholar 

Matzas M., Stähler P.F., Kefer N., Siebelt N., Boisguérin V., Leonard J.T., Keller A., Stähler C.F., Häberle P., Gharizadeh B., Babrzadeh F., Church G.M. 2010. High-fidelity gene synthesis by retrieval of sequence-verified DNA identified using high-throughput pyrosequencing. Nat. Biotechnol. 28 (12), 1291–1294.

CAS  PubMed  PubMed Central  Google Scholar 

Stähler P.F., Carapito R., Stähler C.F., Malzas M., Leonard J.T., Jäger J., Beier M. 2010. WO Patent No. 2010/094772 Al. Geneva: Switzerland World Intellectual Property Organization International Bureau.

Stähler P.F., Carapito R., Stähler C.F., Malzas M., Leonard J.T., Jäger J., Beier M. 2018. US Patent No. US 2017/0267999 A1. Washington, DC: U.S. Patent and Trademark Office.

Lee H., Kim H., Kim S., Ryu T., Kim H., Kwon D.B.S. 2015. A high-throughput optomechanical retrieval method for sequence-verified clonal DNA from the NGS platform. Nat. Commun. 6, 6073.

CAS  PubMed  Google Scholar 

Bang D., Kim H., N., Lim H., Park S., Han H. 2020. US Patent No. 10526640 B2. Washington, DC: U.S. Patent and Trademark Office.

Cho N., Seo H.N., Ryu T., Kwon E., Huh S., Noh J., Yeom H., Byungjin Hwang B., Ha H., Lee J.H., Kwon S., Bang D. 2018. High-throughput construction of multiple cas9 gene variants via assembly of high-depth tiled and sequence-verified oligonucleotides. Nucleic Acids Res. 46 (9), e55.

PubMed  PubMed Central  Google Scholar 

Yeom H., Ryu T., Lee A.C., Noh J., Lee H., Choi Y., Kim N., Kwon S. 2020. Cell-free bacteriophage genome synthesis using low-cost sequence-verified array-synthesized oligonucleotides. ACS Synth. Biol. 9 (6), 1376–1384.

CAS  PubMed  Google Scholar 

Smith J.D., Schlecht U., Xu W., Suresh S., Horecka J., Proctor M.J., Aiyar R.S., Bennett R.A., Chu A., Li Y.F., Roy K., Davis R.W., Steinmetz L.M., Hyman R.W., Levy S.F., St Onge R.P. 2017. A method for high-throughput production of sequence-verified DNA libraries and strain collections. Mol. Syst. Biol. 13 (2), 913.

PubMed 

Comments (0)

No login
gif