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1 l-telluride-thymidine derivatives and the Te-phosphoramidite.
2 two efficient routes from [3-15N]-thymidine phosphoramidite.
3 e-U-RNAs as well as the 2-Se-uridine ((Se)U) phosphoramidite.
4 synthetically from either D- or L-nucleoside phosphoramidites.
5 n moving from Taddol-based to biphenol-based phosphoramidites.
6 s comparable to those of deoxyribonucleoside phosphoramidites.
7 nthesis are comparable to those for standard phosphoramidites.
8 sis of RNA oligonucleotides using nucleoside phosphoramidites.
9 red the synthesis of the appropriate reverse phosphoramidites.
10 hieved with 2-cyanoethyl deoxyribonucleoside phosphoramidites.
11 y.dA were introduced by using the respective phosphoramidites.
12 commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites.
13 )-pteridone (DMAP), have been synthesized as phosphoramidites.
14 the cross-link using protected nucleoside 5'-phosphoramidites.
15 ing of the nucleophile incorporated in these phosphoramidites.
16 the cross-link using protected nucleoside 3'-phosphoramidites.
17 by TBS for the convenience of conversion to phosphoramidites.
18 nctionalized triazole-linked 2'-deoxyuridine phosphoramidites.
19 ipulations to provide the desired pyrimidine phosphoramidites.
25 -1-propyl group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw
30 d in the preparation of four deoxynucleoside phosphoramidites 28 and 65-67, plus the 2'-O-(2-methoxye
34 The most effective ligands identified are phosphoramidite 4, derived from BINOL and N-methylanilin
35 5 mol % Rh(nbd)2BF4, 1.1 mol % BINOL-derived phosphoramidite 4, THF, 40 degrees C, 2 h) affording an
38 synthesis of 3-methylpseudouridine (m(3)Psi) phosphoramidite, 5'-O-[benzhydryloxybis(trimethylsilylox
39 ntermediate, silylated nucleoside amino acid phosphoramidite 6, prepared from a series of reactions s
41 l were incorporated into deoxyribonucleoside phosphoramidites 7a-d and 9, which were found as efficie
42 corporation of activated deoxyribonucleoside phosphoramidite 8b into the oligonucleotide chain during
43 eport we describe a new ferrocene-containing phosphoramidite 9 that provides a range of detectable re
45 for 2'-hydroxyl protection of ribonucleoside phosphoramidites 9a-d has been implemented (Schemes 1 an
46 m a mixture of [3-15N]-labeled thymine dimer phosphoramidites after which the cis-syn dimer-containin
50 ly chiral YanPhos, bearing an N-benzyl BINOL-phosphoramidite and a BINAP-bis(3,5-t-Bu-aryl)phosphine,
51 e, we describe conversion of the ligand to a phosphoramidite and direct incorporation of this moiety
52 a 3-deaza analog of 3MeA (3dMeA) as a stable phosphoramidite and have incorporated the analog into sy
53 nthesized the novel 2'-methylseleno cytidine phosphoramidite and improved the accessibility of the 2'
54 ield of 0.88, and it can be synthesized as a phosphoramidite and incorporated into oligonucleotides t
55 d for the first time the 6-Se-deoxyguanosine phosphoramidite and incorporated it into DNAs via solid-
56 gents through the preparation of a caged DNA phosphoramidite and its site-specific incorporation into
57 synthesizing the novel 4-Se-uridine ((Se)U) phosphoramidite and Se-nucleobase-modified RNAs ((Se)U-R
59 osine, which was converted to the nucleoside phosphoramidite and used in the preparation of oligodeox
60 NPdR can be converted to its 5'-DMTr-3'-CE-phosphoramidite and was incorporated into pentacosanucle
61 mon dimethoxytrityl-protected mononucleotide phosphoramidites and a single orthogonally protected tri
62 taining nucleosides are converted into their phosphoramidites and are utilized for the high-yield pre
63 ese nucleosides were converted to their 3'-O-phosphoramidites and controlled-pore glass solid support
64 osides were converted into the corresponding phosphoramidites and incorporated into oligodeoxynucleot
65 esign, commencing with acyclic amine-derived phosphoramidites and leading to cyclic pyrrolidine and a
67 od is compatible with commercially available phosphoramidites and other oligonucleotide synthesis rea
68 amethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be ef
70 the synthesis of the cMOE and cEt nucleoside phosphoramidites and the biophysical evaluation of oligo
71 yclohexenyl nucleic acid (F-CeNA) pyrimidine phosphoramidites and the synthesis and biophysical, stru
72 lock, the 2'-SeMe-modified guanosine (G(Se)) phosphoramidite, and report the first incorporation of t
76 d into oligomeric DNA using the standard DMT-phosphoramidite approach in an automated solid-phase syn
78 an be further processed to the corresponding phosphoramidite as DNA building blocks that allow incorp
79 By using our own-developed C2-unsymmetric phosphoramidite as supporting ligand, this dipole was ap
80 s with aryl boroxines using a TADDOL-derived phosphoramidite as the ligand provides the corresponding
87 -2-cyclohexen-1-one with the Feringa (S,R,R)-phosphoramidite binaphthol ligand, followed by aldol con
89 nd, the nucleosides 1c and 3c as well as the phosphoramidite building blocks 19 and 23 were prepared
91 l, and pyrenyl)-deoxyguanosine (dG) modified phosphoramidite building blocks and the corresponding da
94 rans, R and S O(6)-allyl-protected N(2)-dGuo phosphoramidite building blocks derived through cis and
95 f the thiosugar into the four ribonucleoside phosphoramidite building blocks was accomplished with ad
98 d using a nucleophilic N-heterocycle-flanked phosphoramidite catalyst in combination with the common
102 s or cis forms of dG-N2-TAM were prepared by phosphoramidite chemical procedure and used as templates
103 oding property of the N(2)-Et-dG DNA adduct, phosphoramidite chemical synthesis was used to prepare s
104 rates using light-directed photolithographic phosphoramidite chemistry and evaluate the stabilities o
105 ive of glycidaldehyde, was synthesized using phosphoramidite chemistry and site-specifically incorpor
106 The oligomers were prepared using automated phosphoramidite chemistry and terminate with a 5'-phosph
107 hesized from the same twisted monomers using phosphoramidite chemistry folded into homodimer and hete
108 ated with bromophosphates or synthesized via phosphoramidite chemistry in moderate yields (44-77%.) T
110 ophobic units are usually attached employing phosphoramidite chemistry involving a DNA synthesizer.
111 ort the synthesis of fdG-modified DNAs using phosphoramidite chemistry involving only three steps.
112 se oligonucleotide synthesis (SPOS) based on phosphoramidite chemistry is currently the most widespre
123 ed HPLC separation method, the four possible phosphoramidites (cis/trans, R/S) of the B[a]P DE-2 N2-d
124 a deoxy-T derivative with the support-bound phosphoramidite compares well with the nucleoside loadin
126 using an achiral catalyst, and then explore phosphoramidite-complexed rhodium catalysts in the enant
127 imidazole catalyzed by metallacyclic iridium-phosphoramidite complexes, in combination with studies o
128 of X-ray structures of rhodium(cod)chloride/phosphoramidite complexes, we have formulated a mechanis
130 hemical element, the catalyst derived from a phosphoramidite containing a biphenolate group was studi
132 ed by a readily available chiral monodentate phosphoramidite-copper complex in the presence of an alk
133 dified nucleosides requires the synthesis of phosphoramidites corresponding to all four canonical bas
136 of two successive chemoselective steps: (i) phosphoramidite coupling, and (ii) radical-radical coupl
139 rmations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable gam
140 , 2'-deoxy-2'-C-methylcytidine (12), and the phosphoramidite derivative of 2'-deoxy-2'-C-beta-methylc
141 Here, we report the first synthesis of the phosphoramidite derivative of dinucleotide SP TpT, which
142 thesis of a novel 2'-O-methyl (OMe) riboside phosphoramidite derivative of the G-clamp tricyclic base
143 the sequence phosphitylated to generate the phosphoramidite derivative on the 5'-terminus of the sup
144 dehalogenase-compatible chloroalkane linker phosphoramidite derivative that enables the rapid automa
145 ynthesized, converted into the corresponding phosphoramidite derivatives and introduced into short ol
146 luene deoxyribosides into suitably protected phosphoramidite derivatives and their incorporation into
147 s could be incorporated readily as protected phosphoramidite derivatives into synthetic oligonucleoti
148 the group II intron, we synthesized six new phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-(hydr
151 thods for the synthesis of five C-nucleoside phosphoramidite derivatives that, when used in combinati
154 lpha-mannosyl and alpha-N-acetyl-glucosamine phosphoramidite derivatives with the serine hydroxyl of
157 way in which the electronic structure of the phosphoramidite dramatically influences reaction rate an
158 ion of two complete series of RNA nucleoside phosphoramidites; each has an appropriately protected am
160 single orthogonally protected trinucleotide phosphoramidite (Fmoc-TAG; Fmoc = 9-fluorenylmethoxycarb
161 p through a multistep process: Reaction with phosphoramidite followed by oxidation provided the 5'-mo
163 2a is amenable to formation of the requisite phosphoramidite for solid-phase oligonucleotide synthesi
164 p route to 5-hydroxymethylcytidine (hm(5)rC) phosphoramidite for solid-phase synthesis of modified RN
165 accessibility of the 2'-methylseleno uridine phosphoramidite for the synthesis of many selenium-deriv
168 lized thymine and 5-methylcytosine amino-LNA phosphoramidites from these key intermediates, respectiv
170 e oligonucleotides, the use of nucleoside 5'-phosphoramidites has not generally been used for the ela
171 otriazol-1-yl)-2'-deoxyinosine 5'-O-DMT 3'-O-phosphoramidite, has been prepared and a preliminary eva
172 fficient as 2-cyanoethyl deoxyribonucleoside phosphoramidites in solid-phase oligonucleotide synthesi
173 any sequence are attainable by synthesizing phosphoramidites in which the hydroxyl groups of the cro
174 is compound has now been synthesized and its phosphoramidite incorporated site-specifically into a de
177 The yields of coupling these Se-nucleoside phosphoramidites into DNA or RNA oligonucleotides were o
179 5'-O-BzH-2'- O -ACE-protected pseudouridine phosphoramidite is reported [BzH, benzhydryloxy-bis(trim
182 sized by coupling cytidylyl-(3',5')-cytidine phosphoramidite isotopomers as the common synthetic inte
183 iphosphorus ligands, consisting of phosphine-phosphoramidites L1 and L2 and phosphine-phosphonites L3
184 rdination in a Pd(II) complex of a phosphine-phosphoramidite ligand 1, which showed excellent enantio
186 hip between the stereochemical elements of a phosphoramidite ligand and the stereoselectivity of irid
187 The original process was conducted with a phosphoramidite ligand containing a resolved 2,2-dihydro
188 ion was the development of a new BINOL-based phosphoramidite ligand containing bulky substitution at
190 a metallacyclic iridium complex containing a phosphoramidite ligand derived from (R)-1-(2-naphthyl)et
193 adium-TMM complex in the presence of a novel phosphoramidite ligand possessing a stereogenic phosphor
194 During catalyst activation, a complex of a phosphoramidite ligand possessing one axial chiral binap
197 sence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high
198 copper catalyst bearing a bulky monodentate phosphoramidite ligand, which is essential for attaining
200 Copper catalyst promotion with both chiral phosphoramidite ligands and a phosphate additive is vita
201 plication of a new class of non-C2-symmetric phosphoramidite ligands derived from pyroglutamic acid f
204 (PinBH) using simple chiral monophosphite or phosphoramidite ligands in combination with Rh(nbd)2BF4.
207 ht into the effects of the structures of the phosphoramidite ligands on the stability of the metallac
216 ew terminus modifiers, bearing, along with a phosphoramidite moiety, one, two or four methoxyoxalamid
218 o different types of building blocks, i.e. a phosphoramidite monomer that also contains an alkyl brom
219 f the 5'-OH group in conventional nucleotide phosphoramidite monomers (i.e. PGA-gated deprotection),
220 a streamlined method for the preparation of phosphoramidite monomers and a single-step deprotection
221 ort we demonstrate the use of photoprotected phosphoramidite monomers for light-directed array synthe
223 NA tether was synthesized with nonnucleotide phosphoramidite monomers using the DNA synthesis chemist
226 5.0 mol % of a readily available monodentate phosphoramidite-Ni complex in ethanol, affording a varie
229 present a solution-phase synthesis based on phosphoramidites of dimers and phenolic cores that produ
232 described above, each of the eight possible phosphoramidite oligonucleotide building blocks (DE-1/DE
234 at can be readily converted to nucleoside 2'-phosphoramidites or 3'-triphosphates for solid-phase and
235 n approach is described, which is based on a phosphoramidite (P-amidite) derived reagent (c-PyPA) obt
236 mer extension products, in which acid-labile phosphoramidite (P-N) bonds replace the 5' phosphodieste
237 hase syntheses, uses no more than 4 equiv of phosphoramidite per phenolic alcohol, and provides routi
238 ich is readily incorporated into RNA via the phosphoramidite, perform well at the guide strand 5'-end
240 l, catalyzed by using axially chiral iridium phosphoramidites PR/S-Ir and cinchona amine is establish
241 methoxytrityl)thymidine N,N-diisopropylamino phosphoramidites protected at P(III) with derivatives of
243 polyphosphates were prepared using iterative phosphoramidite protocols on a polystyrene solid support
244 efficiently use smaller volumes of the probe phosphoramidite, purification of pteridine-containing se
246 -myo-inositol key intermediates, a versatile phosphoramidite reagent was employed in the synthesis of
252 urated imines and isocyanates catalyzed by a phosphoramidite-rhodium complex provides pyrimidinones i
254 onadditive pathway passes through a kappa(2)-phosphoramidite-stabilized Pd(+) intermediate, resulting
255 sis of 2'-O-(o-nitrobenzyl)-3'-thioguanosine phosphoramidite starting from N(2)-isobutyrylguanosine i
257 sulfinyl group for 5'-hydroxyl protection of phosphoramidites, such as 10a-d, may lead to the product
258 ile dimethoxytrityl protecting groups of DNA phosphoramidite synthesis reagents with the requisite sp
259 ents are pure chemical species prepared from phosphoramidites synthesized in a single chemical step f
261 method has been demonstrated by introducing phosphoramidite synthons where N-benzyloxycarbonyl (Z) p
262 dinating pyridine ring into a TADDOL-derived phosphoramidite (TADDOL=alpha,alpha,alpha,alpha-tetraary
263 tinum complexes, including hydroxy-tethered, phosphoramidite-tethered, and monodeoxyribonucleotide-te
264 yrene-labeled P4-P6 was prepared using a new phosphoramidite that allows high-yield automated synthes
265 ere we describe the synthesis of a thymidine phosphoramidite that has the 5'-tethered aldehyde masked
268 meric ligands led to the identification of a phosphoramidite that provided the amination product with
269 ols for 2'-N-methyl-2'-amino-2'-deoxyuridine phosphoramidites that are functionalized at the N2'-posi
270 motivated the development of ribonucleoside phosphoramidites that would exhibit coupling kinetics an
271 iminated by using unequal ratios of the four phosphoramidites, the use of such mixtures does not ensu
272 ted with a known amount of polystyrene-bound phosphoramidite to form a diisopropylamine-DCI salt comp
274 ions, coupling of each 2'-deoxynucleoside 3'-phosphoramidite to the growing oligodeoxynucleotide on t
275 ed a synthetic method for producing glycerol phosphoramidites to create a covalent 10-mer of (poly)gl
277 yl protecting groups for deoxyribonucleoside phosphoramidites to improve the synthesis of oligonucleo
278 n with pseudouridine (Psi) and standard base phosphoramidites to synthesize a 19-nucleotide RNA repre
279 We also describe the use of the protected phosphoramidites to synthesize DNA oligonucleotides cont
280 hesis of biophosphates, catalytic asymmetric phosphoramidite transfer remains largely unexplored for
281 oduced by first incorporating a cross-linked phosphoramidite unit at the 5'-end of an oligonucleotide
285 e, adenine, and guanine) nucleobase-modified phosphoramidites was accomplished on a multigram scale.
286 Synthesis of the FHNA and Ara-FHNA thymine phosphoramidites was efficiently accomplished starting f
287 The synthesis of the cMOE and cEt nucleoside phosphoramidites was efficiently accomplished starting f
289 -2'-O-methyl uridine and cytidine nucleoside phosphoramidites were achieved using glucose as the star
290 sphoramidites and mixtures of diastereomeric phosphoramidites were evaluated in the iridium-catalyzed
293 ly diverse C5-functionalized LNA uridine (U) phosphoramidites were synthesized and incorporated into
296 ning Fapy.dG utilized a reverse dinucleotide phosphoramidite, which also required the synthesis of th
298 tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sia