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PC Linker Phosphoramidite
PC Linker Phosphoramidite, a phosphoramidite compound, is used to incorporate photolytic linkages into oligonucleotides.
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Catalog
BRP-02207
Synonyms
3-(4,4'-Dimethoxytrityl)-1-(2-nitrophenyl)-propan-1-yl-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite; PC linker CE Phoshphoramidite; 1-(O-Ph-NO2)-3-(DMTr)oxypropyl amidite; Phosphoramidous acid, N,N-bis(1-methylethyl)-, 3-[bis(4-methoxyphenyl)phenylmethoxy]-1-(2-nitrophenyl)propyl 2-cyanoethyl ester; 3-[Bis(4-methoxyphenyl)phenylmethoxy]-1-(2-nitrophenyl)propyl 2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite; Phosphoramidous acid, bis(1-methylethyl)-, 3-[bis(4-methoxyphenyl)phenylmethoxy]-1-(2-nitrophenyl)propyl 2-cyanoethyl ester
CAS
168329-40-6
IUPAC Name
3-(bis(4-methoxyphenyl)(phenyl)methoxy)-1-(2-nitrophenyl)propyl (2-cyanoethyl) diisopropylphosphoramidite
Molecular Weight
699.78
Molecular Formula
C39H46N3O7P
Canonical SMILES
N#CCCOP(OC(C=1C=CC=CC1N(=O)=O)CCOC(C=2C=CC=CC2)(C3=CC=C(OC)C=C3)C4=CC=C(OC)C=C4)N(C(C)C)C(C)C
InChI
InChI=1S/C39H46N3O7P/c1-29(2)41(30(3)4)50(48-27-12-26-40)49-38(36-15-10-11-16-37(36)42(43)44)25-28-47-39(31-13-8-7-9-14-31,32-17-21-34(45-5)22-18-32)33-19-23-35(46-6)24-20-33/h7-11,13-24,29-30,38H,12,25,27-28H2,1-6H3
InChIKey
KHOFWXQDBRVNMM-UHFFFAOYSA-N
Purity
≥95%
Appearance
Pale yellow foam
Storage
Store at -20 °C
Symbol
PC Linker-CE Phosphoramidite
Shipping
Dry ice
Chemical Structure:
Reference Reading
1. Wavelength-Dependent, Orthogonal Photoregulation of DNA Liberation for Logic Operations
Ling Sum Liu, Hoi Man Leung, Clément Morville, Hoi Ching Chu, Jing Yi Tee, Alexandre Specht, Frédéric Bolze, Pik Kwan Lo. ACS Appl Mater Interfaces. 2023 Jan 11;15(1):1944-1957. doi: 10.1021/acsami.2c20757.
In this study, we synthesized two phosphoramidites based on 2,7-bis-{4-nitro-8-[3-(2-propyl)-styryl]}-9,9-bis-[1-(3,6-dioxaheptyl)]-fluorene (BNSF) and 4,4'-bis-{8-[4-nitro-3-(2-propyl)-styryl]}-3,3'-di-methoxybiphenyl (BNSMB) structures as visible light-cleavable linkers for oligonucleotide conjugation. In addition to the commercial ultraviolet (UV) photocleavable (PC) linker, the BNSMB linker was further applied as a building component to construct photoregulated DNA devices as duplex structures, which are functionalized with fluorophores and quenchers. Selective cleavage of PC and BNSMB is achieved in response to ultraviolet (UV) and visible light irradiations as two inputs, respectively. This leads to controllable dissociation of pieces of DNA fragments, which is followed by changes of fluorescence emission as signal outputs of the system. By tuning the number and position of the photocleavable molecules, fluorophores, and quenchers, various DNA devices were developed, which mimic the functions of Boolean logic gates and achieve logic operations in AND, OR, NOR, and NAND gates in response to two different wavelengths of light inputs. By sequence design, the photolysis products can be precisely programmed in DNA devices and triggered to release in a selective and/or sequential manner. Thus, this photoregulated DNA device shows potential as a wavelength-dependent drug delivery system for selective control over the release of multiple individual therapeutic oligonucleotide-based drugs. We believe that our work not only enriches the library of photocleavable phosphoramidites available for bioconjugation but also paves the way for developing spatiotemporal-controlled, orthogonal-regulated DNA-based logic devices for a range of applications in materials science, polymers, chemistry, and biology.
