XNA Alphabet

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This table originated in a 2025 publication in Nucleic Acids Research by Drs. Chaput, Egli and Herdewijn entitled “The XNA Alphabet”. Anyone wishing to expand the table is welcome to send their request to Dr. Chaput. Please include a PDF of the published paper along with a ChemDraw structure. Requests should be limited to sugar-modified nucleic acids.

NameAbbreviationStructureCitation
Acyclic phosphonate backboneR-ZNAJournal of the American Chemical Society. 2019. 141, 10844-10851.
S-ZNAJournal of the American Chemical Society. 2019. 141, 10844-10851.
4′-Alkoxy-2′-deoxy
nucleic acid		4′-AlkoxNAOrganic Letters. 2015. 17, 3426-3429.
2′-O-Alkylated
nucleic acid		2′-O-AlkylNAHelvetica Chimica Acta. 1995. 78, 486-504.
Alkyl-2′-deoxy
nucleic acid		2′-AlkNATetrahedron. 2001. 57, 7613-7621.
4′-AlkNABioorganic & Medicinal Chemistry Letters.1999. 
9, 885-890.
5′-AlkNAJournal Organic Chemistry. 1995. 60, 788-789.
D-β-Allo-nucleic acidAlloNAScience. 1999.
284, 2118-2124.
D-β-Altritol
nucleic acid		AltNAChemistry: A European Journal. 1999.
5, 2424-2431.
D-β-Altro-nucleic acidAltroNAScience. 1999.
284, 2118-2124.
2′-Amido
nucleic acid		2′-AmidoNANucleic Acids Research. 1995.
23, 51-57.
Amido-bridged
nucleic acid		AmNAChembiochem. 20102. 13, 2513-2516.
2′-Amino deoxy
nucleic acid		NH2-RNABiochemistry. 1973. 12, 5138-5145.
Aminopropyl
nucleic acid		R-APNAChembiochem.
2005. 6, 2298-2304.
S-APNAChembiochem.
2005. 6, 2298-2304.
Apio
nucleic acid		ApioNAChemical Communication. 2011. 47, 8700-8702.
Arabino
nucleic acid		AraNACanadian Journal of Chemistry. 1989. 67, 831-839.
3′-Arafluoro hexitol
nucleic acid		Ara-FHNAJournal of the American Chemical Society. 2011.
133, 16642-16649.
2′-Azido deoxy
nucleic acid		N3-RNABiochemistry. 1973. 12, 5138-5145.
NameAbbreviationStructureCitation
Bicyclo deoxy
nucleic acid		BcDNAHelvetica Chimica Acta. 1994. 77, 716-744.
Bc[3.2.1]DNAChemistry & Biology. 1998. 5, 209-216.
Bc[3.2.1]amide-DNAChemistry: A European Journal. 2002. 8, 5312-5322.
Bc[4.3.0]DNAEuropean Journal of Organic Chemistry. 2009. 2009, 1153-1162.
2′,3′-BcNAJournal of the Chemical Society, Perkin Transactions. 1997. 1, 3423-3433.
Butyl
nucleic acid		BuNAOrganic & Biomolecular Chemistry. 2013. 11, 5853-5865.
NameAbbreviationStructureCitation
Carbocyclic
nucleic acid		carDNANucleic Acids Research. 1990. 18, 2133-2140.
carRNANucleic Acids Research. 1990. 18, 2133-2140.
Cyclohexanyl
nucleic acid		CNAChemistry: A European Journal. 1999. 5, 2139-2150.
D-ribo-Cyclohexanyl
nucleic acid		r-CNAOrganic & Biomolecular Chemistry. 2015. 13, 10041-10049.
Cyclohexenyl
nucleic acid		D-CeNAJournal of the American Chemical Society. 2000. 122, 8595-8602.
L-CeNANucleosides, Nucleotides, Nucleic Acids. 2003. 22, 845-847.
NameAbbreviationStructureCitation
Deoxyribose
nucleic acid  		α-D-DNARoyal Society of Chemistry Advance. 2019. 9, 14302-14320. 
β-D-DNA
(Natural)
β-L-DNA
(mirror image DNA)		Journal of the American Chemical Society. 1991. 113, 8174-8175.
2′,5′-DNA
(MetaDNA)		Journal of the American Chemical Society. 1992. 114, 6255-6256.
Diethanol amide
nucleic acid		DEANAOrganic & Biomolecular Chemistry. 2015. 13, 9249-9260.
2,4-Dihydroxycyclohexyl nucleic acid2,4-DHCNAHelvetica Chimica Acta. 2005. 88, 3210-3224.
Di-O-Methylated altropyranoside
nucleic acids		DMANAMolecules. 2015. 20, 4020-4041.
Disaccharide
nucleic acid		DiNAHelvetica Chimica Acta. 2000. 83, 1278 – 1289.
Disubstituted
deoxy nucleic acid		2′,4′-DFNAAmerican Chemical Society Chemical Biology. 2015. 10, 2016-2023.
  2’F,4’-OMe NA  Journal of the American Chemical Society. 2017. 139, 14542-14555.
  2’OMe,4’F NA  Nucleic Acid Therapeutics. 2019. 29, 187-194.
  2’,4’-diOMe NA  Nucleic Acid Therapeutics. 2019. 29, 187-194.
Double-headed
nucleic acid		2′-DhNAChemical Communication. 2021. 57, 9128-9131.
Double coding
nucleic acid		DcDNAJournal of Organic Chemistry. 2006. 71, 5423-5431.
NameAbbreviationStructureCitation
Ethinyl
nucleic acid		ENABioorganic & Medicinal Chemistry Letters. 1998. 8, 521-524.
Ethylene bridged
nucleic acid		EBNABioorganic & Medicinal Chemistry Letters. 2002. 12, 73-76.
Extended
nucleic acid		ExNANature Biotechnology. 2024.
43, 904–913 (2025).
NameAbbreviationStructureCitation
Ferrocene
nucleic acid		FeNAChemical Communication. 2012. 48, 12165-12167.
Flexible
nucleic acid		FNAProceedings of the National Academy of Sciences of the USA. 1987. 84, 4398-4402.
2′-Fluoro arabino
nucleic acid		FANAJournal of the American Chemical Society. 1998. 120, 12976-12977.
6′-Fluoro[4.3.0]bicyclo nucleic acid6′-F-bc[4.3.0]DNAThe Journal of Organic Chemistry. 2014. 79, 1271-1279.
3′-Fluoro hexitol
nucleic acid		FHNAJournal of the American Chemical Society. 2011.
133, 16642-16649.
FMHNABiochemistry. 2012. 51, 7-9.
Fluoro cyclohexenyl
nucleic acid		F-hJournal of the American Chemical Society. 2000. 122, 8595-8602.
2′-Formamido
nucleic acid		2′-Formamido NANucleic Acids Research. 2024. 52, 10754-10774.
2′-Fluoro
nucleic acid		F-RNAJournal of the American Chemical Society. 1961. 83, 5030-5031.
NameAbbreviationStructureCitation
Glycerol
nucleic acid		GNAJournal of the American Chemical Society. 2005. 127, 4174-4175.
Glycol carbamate
nucleic acid		R-GCNABioorganic & Medicinal Chemistry Letters. 2014. 22, 6227-6232.
S-GCNABioorganic & Medicinal Chemistry Letters. 2014. 22, 6227-6232.
D-β-Gluco
nucleic acid		GlucoNAScience. 1999. 284, 2118-2124.
Glucosamino
nucleic acid		3′,6′-GANABioorganic & Medicinal Chemistry Letters. 2018. 28, 3174-3176.
4′,6′-GANABioorganic & Medicinal Chemistry Letters. 2018. 28, 3174-3176.
NameAbbreviationStructureCitation
Hexitol
nucleic acid		α-L-HNAChemistry: A European Journal. 2009. 15, 10121-10131.
α-D-HNAOrganic Letters. 2001. 3, 4129-4132.
β-L-HNAThe Journal of Organic Chemistry. 2015. 80, 5014-5022.
β-D-HNAChemistry: A European Journal. 1997. 3, 110-120.
Homo-N-deoxyribose nucleic acidα-D–Homo-DNAChemistry: A European Journal. 2001. 7, 5183-5194.
β-D-Homo-DNABioorganic & Medicinal Chemistry Letters. 1992. 2, 945-948.
β-L-Homo-DNAThe Journal of Organic Chemistry. 2010. 75, 6402-6410.
1′-homoDNABioorganic & Medicinal Chemistry Letters. 1996. 6, 1465-1468.
Hydroxy-N-acetylprolinol nucleic acidHydroxy-N-AcProNATetrahedron. 1997. 53, 14957-14974.
3′-Hydroxymethyl – aldopentopyranose
nucleic acid		3′-hmAPPNATetrahedron. 1995. 51, 12319-12336.
5′-Hydroxyphosphonate-linked nucleic acid5′-hpDNANucleic Acids Research. 2014. 42, 5378-5389.
NameAbbreviationStructureCitation
Intercalating
nucleic acid		INANucleic Acids Research. 2002. 30, 4918-4925.
Isobicyclo
deoxy nucleic acid		IsoBcDNAChemistry: A European Journal. 2013. 19, 6990-7006.
Iso-glycerol
nucleic acid		IsoGNAAngewandte Chemie International Edition. 2013. 52, 5840-5844.
NameAbbreviationStructureCitation
Locked
nucleic acid		LNAJournal of the American Chemical Society. 1998. 120, 13252-13253.
α-LNA
(α-Locked NA)		Journal of the American Chemical Society. 2002. 124, 2164-2176.
Methylene-cLNA
(Methylene-
carbocyclo LNA)		Journal of the American Chemical Society. 2010. 132, 14942-14950.
cEt BNA
(Cyclic 2′-O-Ethyl LNA)		The Journal of Organic Chemistry. 2010. 75, 1569-1581.
cMOENA (2′-O-Methoxyethyl LNA)Journal of Medicinal Chemistry. 2009. 52, 10-13.
Lyxo
nucleic acid		2′,4′-LyxoNAScience. 1999. 284, 2118-2124.
3′,4′-LyxoNAScience. 1999. 284, 2118-2124.
NameAbbreviationStructureCitation
Mannitol
nucleic acid		ManNAThe Journal of Organic Chemistry. 1998. 63, 1574-1582.
Methanocarba
nucleic acid		NMDNA
(North Methanocarba
DNA)		Chembiochem. 2011. 12, 1056-1065.
SMDNA
(South methanocarba
DNA)		Tetrahedron Letters. 1994. 35, 7625-7628.
2′-O-Methoxyethyl
nucleic acid		MOENAHelvetica Chimica Acta. 1995. 78, 486-504.
3′-O-Methylated ANAMANANucleic Acids Research. 2001. 29, 4187-4194.
Morpholino
nucleic acid		MorphNA
(PMO)		Antisense Nucleic Acid Drug Development. 1997. 7, 187-195.
NameAbbreviationStructureCitation
Oxepane
nucleic acid		OxNAJournal of the American Chemical Society. 2007. 129, 8259-8270.
NameAbbreviationStructureCitation
Peptide
nucleic acid		PNAThe Journal of Organic Chemistry. 1994. 59, 5767-5773.
Phosphoramidate
nucleic acid		N3’→N5′-DNAProceedings of the National Academy of Sciences of the USA. 1995. 92, 5798-5802.
Polycarbamate
nucleic acid		PCNAOrganic & Biomolecular Chemistry. 2010. 8, 3734-3741.
Prolinol
nucleic acid		ProNAChemistry: A European Journal. 1997. 3, 1997-2010.
NameAbbreviationStructureCitation
Ribose
nucleic acid		D-RNA (natural) 
L-RNA
(mirror image RNA)		Journal of the American Chemical Society. 1992. 114, 9731-9736.
2′,5′-RNA
(MetaRNA)		Nucleic Acids Research. 1992. 20, 1685-1690.
Ribulo
nucleic acid		RibuloNAChemistry. 2018. 24, 12811-12819.
NameAbbreviationStructureCitation
Serinol
nucleic acid 		SNAAngewandte Chemie International Edition. 2011. 50, 1285-1288.
NameAbbreviationStructureCitation
4′ Thio
nucleic acid		4′-ThioDNANucleic Acids Research. 2006. 34, 3476-3483. 
4′-ThioRNANucleosides, Nucleotides, & Nucleic Acids. 1995. 14, 1027-1030.
  α-L-threofuranosyl
nucleic acid		TNAScience. 2000. 290, 1347-1351.
Threoninol
nucleic acid 		a-D-TNAChemical Communication. 2015. 51, 6500-6503.
a-L-TNAChemical Communication. 2015. 51, 6500-6503.
Tricyclo
nucleic acid		TricycloDNAJournal of the American Chemical Society. 1999. 121, 3249-3255.
Triethyl amino
nucleic acid		TEANAOrganic & Biomolecular Chemistry. 2015. 13, 9249-9260.
NameAbbreviationStructureCitation
Unlocked
nucleic acid		UNABioorganic & Medicinal Chemistry Letters. 1995. 3, 19-28.
NameAbbreviationStructureCitation
Vinylpropyl
nucleic acid		VPNANucleic Acids Research. 2021. 49, 12069-12088.
NameAbbreviationStructureCitation
W-shape
nucleic acid		WNATetrahedron Letters. 2001. 42, 6915-6918.
NameAbbreviationStructureCitation
Xylo
nucleic acid		XyloNA
Nucleic Acids Research. 2015. 43, 7189-7200.
Deoxyxylo
nucleic acid		dXyloNA
Helvetica Chimica Acta. 1991. 74, 748-760.