7. Backbone Modification 核酸分子骨架修饰

7.1. Peptide Nucleic Acids (PNA)

PNAs are oligonucleotide analogues in which the standard sugar-phosphate backbone of DNA is substituted by a pseudo-peptide backbone. They were invented in 1991 by a group of scientists at the University of Copenhagen: Prof. Peter E. Nielsen, Prof. Ole Buchardt, Dr. Michael Egholm, and Dr. Rolf H. Berg (PNA Inventor Group). PNAs hybridise strongly and sequence-specifically to complementary DNA or RNA, however they are not degraded by nucleases or proteases. Such properties have made PNA the subject of great scientific interest and synthetic PNA oligomers have numerous identified and proposed applications in molecular biology procedures, diagnostic assays, as well as antisense and anti-gene therapies.
After extensive screening, the benzhydryloxycarbonyl (Bhoc) group was selected as the best choice for protecting the exocyclic amino groups of the nucleobases. This group provides sufficient protection during synthesis, is readily removed under the cleavage conditions, and renders solubility to the monomers. For PNA synthesis, therefore, we provide the four Fmoc/Bhoc monomers and a spacer molecule.
Fmoc-PNA-A(Bhoc)-OH
N-((N6-(Benzhydryloxycarbonyl)aden-9-yl)acetyl)-N-(2-Fmoc-aminoethyl)glycine

• Item Number: 5001
• Formula: C₄₀H₃₅N₇O₇
• Formula Weight: 725.76
• Unit Weight: 275.27

Fmoc-PNA-C(Bhoc)-OH
N-((N4-(Benzhydryloxycarbonyl)cytosin-1-yl)acetyl)-N-(2-Fmoc- aminoethyl)glycine

• Item Number: 5002
• Formula: C₃₉H₃₅N₅O₈
• Formula Weight: 701.74
• Unit Weight: 251.24

Fmoc-PNA-G(Bhoc)-OH
N-((N2-(Benzhydryloxycarbonyl)guan-9-yl)acetyl)-N-(2-Fmoc-aminoethyl)glycine

• Item Number: 5003
• Formula: C₄₀H₃₅N₇O₈
• Formula Weight: 741.76
• Unit Weight: 291.27

Fmoc-PNA-T-OH
N-(Thymin-1-ylacetyl)-N-(2-Fmoc-aminoethyl)glycine

• Item Number: 5004
• Formula: C₂₆H₂₆N₄O₇
• Formula Weight: 506.52
• Unit Weight: 266.26

Fmoc-AEEA-OH Spacer
[2-(2-(Fmoc-amino)ethoxy)ethoxy]acetic acid

• Item Number: 5005
• Formula: C₂₁H₂₃NO₆
• Formula Weight: 385.42
• Unit Weight: 145.16

7.2. Unlocked Nucleic Acids (UNA)

Ac-C-UNA-CE Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-acetyl-2',3'-seco-cytosine, 2'-benzoyl- 3'-[(2-cyanoethyl)-(N,N- diisopropyl)]-phosphoramidite

• Item Number: 2184
• Formula: C₄₈H₅₆N₅O₁₀P
• Formula Weight: 893.97
• Unit Weight: 307.20

U-UNA-CE Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-2',3'-seco-uridine, 2'-benzoyl-3'-[(2- cyanoethyl)-(N,N- diisopropyl)]-phosphoramidite

• Item Number: 2186
• Formula: C₄₆H₅₃N₄O₁₀P
• Formula Weight: 852.92
• Unit Weight: 308.18

Bz-A-UNA-CE Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-benzoyl-2',3'-seco-adenosine, 2'- benzoyl-3'-[(2-cyanoethyl)-(N,N- diisopropyl)]-phosphoramidite

• Item Number: 2183
• Formula: C₅₄H₅₈N₇O₉P
• Formula Weight: 980.07
• Unit Weight: 331.23

iBu-G-UNA-CE Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-isobutyryl-2',3'-seco-guanosine, 2'- benzoyl-3'-[(2-cyanoethyl)-(N,N- diisopropyl)]-phosphoramidite

• Item Number: 2185
• Formula: C₅₁H₆₀N₇O₁₀P
• Formula Weight: 962.05
• Unit Weight: 347.23

7.3 Methyl Phosphonamidites

Bz-dA-Me Phosphonamidite
5'-(4,4'-Dimethoxytrityl)-N-benzoyl-2'-deoxyadenosine, 3'-[methyl- (N,N-diisopropyl)]-phosphonamidite

• Item Number: 2075
• Formula: C₄₅H₅₁N₆O₆P
• Formula Weight: 802.91
• Unit Weight: 311.24

Ac-dC-Me Phosphonamidite
5'-(4,4'-Dimethoxytrityl)-N-acetyl-2'-deoxycytidine, 3'-[methyl- (N,N-diisopropyl)]-phosphonamidite

• Item Number: 2077
• Formula: C₃₉H₄₉N₄O₇P
• Formula Weight: 716.81
• Unit Weight: 287.21

iBu-dG-Me Phosphonamidite
5'-(4,4'-Dimethoxytrityl)-N-isobutyryl-2'-deoxyguanosine, 3'- [methyl-(N,N-diisopropyl)]-phosphonamidite

• Item Number: 2074
• Formula: C₄₂H₅₃N₆O₇P
• Formula Weight: 784.89
• Unit Weight: 327.24

dT-Me Phosphonamidite
5'-(4,4'-Dimethoxytrityl)-thymidine, 3'-[methyl-(N,N-diisopropyl)]- phosphonamidite

• Item Number: 2073
• Formula: C₃₈H₄₈N₃O₇P
• Formula Weight: 689.79
• Unit Weight: 302.23

Pac-dA-Me Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-phenoxyacetyl-2'-deoxyadenosine, 3'- [methyl-(N,N-diisopropyl)]-phosphoramidite

• Item Number: 2052
• Formula: C₄₆H₅₃N₆O₈P
• Formula Weight: 848.93
• Unit Weight: 327.23 (Me triester)

Ac-dC-Me Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-acetyl-2'-deoxycytidine, 3'-[methyl- (N,N-diisopropyl)]-phosphoramidite

• Item Number: 2050
• Formula: C₃₉H₄₉N₄O₈P
• Formula Weight: 732.81
• Unit Weight: 303.21 (Me triester)

iPr-Pac-dG-Me Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-(4-isopropylphenoxyacetyl)-2'-deoxyguanosine, 3'- [methyl-(N,N-diisopropyl)]-phosphoramidite

• Item Number: 2051
• Formula: C₄₉H₅₉N₆O₉P
• Formula Weight: 907.01
• Unit Weight: 343.23 (Me triester)

dT-Me Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-thymidine, 3'-[methyl-(N,N-diisopropyl)]- phosphoramidite

• Item Number: 2078
• Formula: C₃₈H₄₈N₃O₈P
• Formula Weight: 705.79
• Unit Weight: 318.22 (Me triester)

7.4 H-Phosphonates

Bz-dA-H-Phosphonate, TEA Salt
5'-(4,4'-Dimethoxytrityl)-N-benzoyl-2'-deoxyadenosine, 3'-H-phosphonate, triethylammonium salt

• Item Number: 2007
• Formula: C₄₄H₅₁N₆O₈P
• Formula Weight: 822.90
• Unit Weight: 313.21

Bz-dC-H-Phosphonate, DBU salt
5'-(4,4'-Dimethoxytrityl)-N-benzoyl-2'-deoxycytidine, 3'-H-phosphonate, diazabicycloundecene salt

• Item Number: 2035
• Formula: C₄₆H₅₂N₅O₉P
• Formula Weight: 849.93
• Unit Weight: 289.18

iBu-dG-H-Phosphonate, TEA salt
5'-(4,4'-Dimethoxytrityl)-N-isobutyryl-2'-deoxyguanosine, 3'- H-phosphonate, triethylammonium salt

• Item Number: 2006
• Formula: C₄₁H₅₃N₆O₉P
• Formula Weight: 804.89
• Unit Weight: 329.21

dT-H-Phosphonate, TEA salt
5'-(4,4'-Dimethoxytrityl)-thymidine, 3'-H-phosphonate, triethylammonium salt

• Item Number: 2005
• Formula: C₃₇H₄₈N₃O₉P
• Formula Weight: 709.79
• Unit Weight: 304.20

7.5 Sulphurisation

Sulphurising Reagent (Beaucage)
3H-1,2-Benzodithiole-3-one-1,1-dioxide

• Item Number: 0023
• Formula: C₇H₄O₃S₂
• Formula Weight: 200.23

This product is supplied with a silanised bottle (free of charge) for use in the dilution of the product. Either ABI/MerMade and Expedite compatible bottles can be supplied therefore when ordering please also order the apporopriate bottle (see related products opposite).

EDITH

3-Ethoxy-1,2,4-dithiazoline-5-one

• Item Number: 2171
• Formula: C₄H₅NO₂S₂
• Formula Weight: 163.21

EDITH is available in millimolar pack sizes, ready for convenient dilution, in a bottle of your choice,to 0.05M with anhydrous acetonitrile (5mmol/100ml, 10mmol/200ml, and 22.5mmol/450ml).
If demand is there from our customers we will also provide EDITH packaged in synthesier-ready bottles (ABI, Expedite, MerMade). Please contact us if this is your preferred option.
Please contact us for bulk packaging and pricing.
The use of EDITH in the US is protected under US Patent No. 5,852,168 and licence must be sought from The University of Minneapolis.

7.6 Ethyl Phosphoramidites

Bz-dA Ethyl Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-benzoyl-2'-deoxyadenosine, 3'-[(2- ethyl)-(N,N-diisopropyl)]-phosphoramidite

• Item Number: 2518
• Formula: C₄₆H₅₃N₆O₇P
• Formula Weight: 832.94
• Unit Weight: 342.27 (with Et) or 313.21 (without)

Bz-dC Ethyl Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-benzoyl-2'-deoxycytidine, 3'-[(2- ethyl)-(N,N-diisopropyl)]-phosphoramidite

• Item Number: 2519
• Formula: C₄₅H₅₃N₄O₈P
• Formula Weight: 808.91
• Unit Weight: 318.24 (with Et) or 289.18 (without)

iBu-dG Ethyl Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-N-isobutyryl-2'-deoxyguanosine, 3'- [(2-ethyl)-N,N-diisopropyl]-phosphoramidite

• Item Number: 2517
• Formula: C₄₃H₅₅N₆O₈P
• Formula Weight: 814.92
• Unit Weight: 358.27 (with Et) or 329.21 (without)

dT Ethyl Phosphoramidite
5'-(4,4'-Dimethoxytrityl)-thymidine, 3'-[(2-ethyl)-N,N-diisopropyl]- phosphoramidite

• Item Number: 2516
• Formula: C₃₉H₅₀N₃O₈P
• Formula Weight: 719.82
• Unit Weight: 333.26 (with Et) or 304.20 (without)

Product	Pack Size	Cat No.
Bz-dA Ethyl Phosphoramidite	500mg	2518-B500
	1g	2518-C001
Bz-dC Ethyl Phosphoramidite	500mg	2519-B500
	1g	2519-C001
iBu-dG Ethyl Phosphoramidite	500mg	2517-B500
	1g	2517-C001
dT Ethyl Phosphoramidite	500mg	2516-B500
	1g	2516-C001