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1 arly critical residue in AIP-II, however, is exocyclic.
3 and the lack of cross-link formation by the exocyclic 1,N(2)-dG adduct of (6R,8S,11R) stereochemistr
4 ccordingly, the chemistry of the HNE-derived exocyclic 1,N(2)-dG adduct of (6S,8R,11S) stereochemistr
5 rmation of the interstrand cross-link by the exocyclic 1,N(2)-dG adduct of (6S,8R,11S) stereochemistr
7 acrolein- and the 6R-crotonaldehyde-derived exocyclic 1,N(2)-dG adducts form interstrand N(2)-dG:N(2
9 ponding acrolein- and crotonaldehyde-derived exocyclic 1,N(2)-dG adducts undergo ring-opening to N(2)
12 its two gamma positions to form the isomeric exocyclic (1-exo) and endocyclic (1-endo) dienolates.
13 benzo-[a]pyrene 7,8-diol 9,10-epoxide by the exocyclic 2-amino group of deoxyguanosine at specific po
14 lized through the intermediacy of an unknown exocyclic [7,10:1,5]patchoul-4(12)-ene (15-d(1)), which
15 ehyde and is known to react with DNA forming exocyclic acrolein-deoxyguanosine adducts (Acro-dG).
16 analyses show that the hydrogenation of the exocyclic activated C horizontal lineC double bond has a
17 s of this class includes the position of the exocyclic acyl group, the prenylation grade of the core,
18 thynyl]phenyl rod that is separated from the exocyclic acylcarbonyl of the DAG-lactone core by a spac
22 ethyl)-3,N(4)-etheno-C (8-HM-epsilonC) is an exocyclic adduct resulting from the reaction of dC with
24 stress that reacts with guanine to form the exocyclic adduct, pyrimido[1,2- alpha]purin-10(3H)-one (
26 n DNA lesions and the enzyme, the effects of exocyclic adducts on DNA cleavage mediated by human topo
27 Together, these data suggest that multiple exocyclic adducts undergo oxidation and glycolytic cleav
31 e RT dNTP binding site that accommodates the exocyclic alkene moiety of ETV was predicted, establishi
33 ated with alkene transposition to afford the exocyclic alkene; alternatively, the reactivity of the c
34 he 3,3-difluoro-2,4-dione intermediates gave exocyclic alkenes that underwent hydrogenation accompani
35 losing metathesis to afford the synthesis of exocyclic allylic amines from their endocyclic precursor
36 ment with allylic transposition yielding the exocyclic allylsilane 3a with excellent diastereoselecti
37 ray crystal structure of DHO showed that the exocyclic alpha-carboxylate of dihydroorotate is bound t
38 region in the resulting product contains an exocyclic amide positioned alpha to the peptide backbone
39 sely, adding the equivalent of adenine's C-6 exocyclic amine (N-6) to 1- and 3-deazapurines also enha
41 e local DNA environment and proximity of the exocyclic amine determine the selectivity for reaction w
42 o metabolic activation by N-oxidation of the exocyclic amine group to produce N-hydroxylated metaboli
43 h bioactivate HAAs by N-hydroxylation of the exocyclic amine group; the resultant N-hydroxy-HAA metab
44 at lacks the N4 amino group, implicating the exocyclic amine in critical interactions in the active s
45 terification rate, implying that the guanine exocyclic amine is not a critical determinant of DNA cle
46 the addition of a dimethylallyl group to the exocyclic amine nitrogen (N6) of A(37) in several tRNA s
47 specially sensitive to changes involving the exocyclic amine of A756; by contrast, the cleavage activ
48 a combination of hydrogen bonding to the N6 exocyclic amine of adenosine and steric exclusion of the
49 A pair is in an imino conformation where the exocyclic amine of G contributes approximately 1.4 kcal/
50 ronment and provided a rationale for how the exocyclic amine of nucleobase 8 promotes productive, in-
52 th steps; moreover, proton transfer from the exocyclic amine of protonated C75 to the nonbridging oxy
53 drogen bond between the formyl group and the exocyclic amine of the 3'-neighbor adenine stabilizes th
54 en bonding between the formyl oxygen and the exocyclic amine of the 3'-neighboring adenine stabilizin
55 esence of a unique hydrogen bond between the exocyclic amine of the inhibitor and threonine 106 which
56 phospholane approach, which does not require exocyclic amine protection of the nucleobase, has been s
57 through hydrogen bond formation between the exocyclic amine protons of G(7) and the (iPr)Th nitrogen
58 denosine receptor (A3AR) agonists lacking an exocyclic amine resulted from an unexpected reaction dur
61 can partially compensate for the lack of an exocyclic amine, an otherwise important contributor to r
64 m correlation (NOESY-HSQC) NMR, in which the exocyclic amines at X(7) or Y(19) were (15)N-labeled.
67 ine (Dma), which we show to remain intact on exocyclic amines of adenine bases while other bases carr
69 hat binds the AIP thiolactone ring while the exocyclic amino acid tail interacts with loop 1 to facil
70 the determination of the contribution of the exocyclic amino group "N2" of the guanine base to nucleo
71 no selective, total syntheses of the stable exocyclic amino group adducts formed by the single-elect
74 Evidently, tertiary interactions with the exocyclic amino group of a G in a single G.A pair can in
75 observed a distance between fluorine and the exocyclic amino group of A that is consistent with a H-b
78 which supports that the deprotonation at the exocyclic amino group of cytosine cation radical is esse
80 tral G clearly shows the crucial role of the exocyclic amino group of G in sequence-specific recognit
81 (DE) adducts of benzo[a]pyrene (BaP) at the exocyclic amino group of G(+1) block cleavage at a prefe
82 )-anti-benzo[a]pyrene diol epoxide, with the exocyclic amino group of guanine ((+)-trans-anti-[BP]-N(
84 ne diol epoxide, which can attack DNA at the exocyclic amino group of guanine to form the major (+)-t
85 h DNA predominantly by trans addition at the exocyclic amino group of guanine to yield 10S (+)- and 1
88 etermined that the hydrogen bond between the exocyclic amino group of guanosine and the 2'-hydroxyl g
89 o probe the putative interaction between the exocyclic amino group of the guanosine nucleophile and t
90 nd DNA-DNA cross-links via reaction with the exocyclic amino group on a nearby 2-deoxyguanosine or 2-
91 try analysis revealed that Scabin labels the exocyclic amino group on guanine bases in either single-
98 introduced by means of a ring closure of the exocyclic amino groups of a pyrimidinone using [13C]sodi
100 ntaining intrastrand cross-links between the exocyclic amino groups of adjacent deoxyguanosines has b
102 in antagonist CGS15943 1 overlapped, and the exocyclic amino groups of each were H-bonded to the side
103 distortions of the DNA duplexes, because the exocyclic amino groups of flanking guanines on both stra
104 ronmental carcinogen benzo[a]pyrene), to the exocyclic amino groups of guanine or adenine in oligonuc
105 zo[a]pyre ne {B[a]P DE-2 (2)} at C-10 by the exocyclic amino groups of protected purine nucleosides i
106 enanthrene, reacts with DNA primarily at the exocyclic amino groups of purines, forming B[c]PhDE-DNA
107 sented here show that M(1)dG and its stable, exocyclic analog 1,N(2)-propanodeoxyguanine (PdG), arres
110 tailed investigation of the influence of the exocyclic base adduct on the overall helical structure a
111 ed the possibility that structurally similar exocyclic base adducts may be good candidates for enzyma
113 oted more ozone reactions with the remaining exocyclic bond of oxidized limonene products in the SOA
116 nal monomer, contains both a highly reactive exocyclic C horizontal lineC bond and a highly stable fi
117 e E or E,E configuration with respect to the exocyclic C horizontal lineC bond is stabilized by inter
118 etween the electron donor groups (oxygen and exocyclic C horizontal lineC double bond) and CH bonds o
119 ose predictable conformational biases on the exocyclic C-5-C-6 bond, as determined by (1)H-(1)H and (
121 tributed to a rotation around one of the two exocyclic C-C bonds bridging phenol and imidazolinone gr
123 sugars for the most part) suggests that the exocyclic C-O bond in acetate esters of cyclic alcohols
125 nd transition states for rotation around the exocyclic C==N bond, electrocyclic ring closure, and los
126 r-catalyzed addition of ZnEt2 (ZnBu2) to the exocyclic C=C bond of pentafulvenes C5H4(=CHAr) (Ar=2-Me
128 ) with 2'-deoxyinosine (dI), which lacks the exocyclic C2 amino group present in dG, also prevented D
130 of NAD(P)H is transferred to the unsaturated exocyclic C6 carbon of HMMF, resulting in a cyclic achir
133 rization to occur, while substitution at the exocyclic carbon atom has an impact on the reaction path
135 dding electron-withdrawing CF3 groups to the exocyclic carbon of this meta-disubstituted benzyl catio
136 Substitution of both oxygen atoms in the exocyclic carbonyl groups of the thymine chromophore by
137 Core characteristics of the series are an exocyclic carbonyl moiety as a hydrogen bond acceptor an
138 to utilize multiple J-couplings sensitive to exocyclic CH(2)OH conformation, the ensemble of experime
139 ulfide bond were observed in addition to the exocyclic cleavages typically seen from CID of [M + nH](
140 2 dihedral, and a greater sampling of non-TG exocyclic conformations, particularly the GG conformatio
144 ns suggest that substituents proximal to the exocyclic COOH group (i.e., the C4-O4 bond) influence th
146 rates a mixture of 3E- and 3Z-olefins of the exocyclic-Delta(3),Delta(5)-dihydrohydroxyphenylpyruvate
147 uted cyanoolefins BTF and TCNE to add to the exocyclic diene portion of 1-isopropenyl-1,3-cyclopentad
148 ient of 0.5, these results indicate that the exocyclic dienolate is 3.0 kcal/mol more stable than its
149 mammalian cells, reacts with DNA to form an exocyclic DNA adduct, 3H-8-hydroxy-3-(beta-D-2'-deoxyrib
150 pair by Escherichia coli AlkB dioxygenase of exocyclic DNA adducts 3,N(4)-ethenocytosine, 1,N(6)-ethe
152 thenoguanine (N(2),3-epsilonG) is one of the exocyclic DNA adducts produced by endogenous processes (
154 mary, our data suggest that acrolein-induced exocyclic DNA lesions can be bypassed by mitochondrial D
160 re made by dihalocarbene addition across the exocyclic double bond of readily accessible 3-alkylidene
161 n addition, gem-dimethyl substitution on the exocyclic double bond of the 2-methyleneaziridine is tol
162 nduced enzyme catalyzes the reduction of the exocyclic double bond of the highly reactive precursor 4
164 ing nitrogen with concurrent formation of an exocyclic double bond to an alpha-carbon of the ring.
165 nd carboxyl group (6) as substituents at the exocyclic double bond was synthesized in the form of the
166 consisting of (1) oxidative cleavage of the exocyclic double bond, (2) stereoselective alpha-methyla
167 ylene in a formal [2+2] cycloaddition at the exocyclic double bond, followed by retroelectrocyclizati
172 we synthesized two new nitroxides bearing an exocyclic double bond: 4-methoxycarbonylmethylidene-2,2,
173 pinene and terpinine, where the isomers with exocyclic double bonds are more highly retained than tho
177 thiomorpholinochlorin with acid converts the exocyclic double bonds to direct links to the ortho-posi
179 ) have been synthesized from the reaction of exocyclic enaminoketones 8 with amines or metalloenamine
180 three major products were identified as the exocyclic, endocyclic, and 4(20)-methylene 7-fluoroverti
185 GSH reacts at the exomethylene carbon of the exocyclic enone, displacing the first GSH to give the fi
189 nd the ability to trap kinetically competent exocyclic enones in aqueous acid using COMC-6 and COMC-7
190 g product profiles which include the desired exocyclic ether, a SiMe(3)-eliminated exocyclic ether, a
191 esired exocyclic ether, a SiMe(3)-eliminated exocyclic ether, and the SiMe(3)-O-functionalized substr
193 LYP/6-31+G(d,p) levels show the formation of exocyclic ethylenes to proceed (a) on the singlet surfac
196 enerated by thiyl radical addition to C4'C5' exocyclic glycals has been re-examined and found to be a
198 s between the equivalent of both N-1 and the exocyclic group at C-6 of a purine NTP (2-fluoroadenine,
199 rate puckering conformations and the role of exocyclic groups have not yet been thoroughly addressed.
201 losing base pair showed that the presence of exocyclic groups in the major groove of purines 3' to th
204 ructure and to evaluate the influence of the exocyclic groups, Density Functional Theory (DFT) calcul
207 ramolecular interactions between consecutive exocyclic hydroxyl groups, which are stable in nonpolar
208 on and nearby protons and carbons within the exocyclic hydroxymethyl group (CH(2)OH) of each compound
211 the resulting product further oxidizes to an exocyclic iminium ion (by the perferryl-oxygen complex);
215 eske aromatic oxygenases, DMO oxygenates the exocyclic methyl group, rather than the aromatic ring, o
216 in the two resulting diols, unmasking of an exocyclic methylene group at C-11, and stereocontrolled
219 al and carboxylic acid analogs containing an exocyclic methylene instead of an epoxide, indicating th
225 ske non-heme iron oxygenase that performs an exocyclic monooxygenation, incorporating O(2) into a sid
226 ter metabolic activation, can react with the exocyclic N (2) amino group of guanine to generate four
227 Further support for the importance of the exocyclic N(2)-amino group in this reaction was provided
229 mutagenicity of trans-opened adducts at the exocyclic N(2)-amino group of guanine by the (+)-(7R,8S,
230 obenzo[a]pyr ene is covalently bonded to the exocyclic N(6)() amino group of the central deoxyadenosi
234 group substitution at G33 indicates that its exocyclic N2 interacts directly with the scissile phosph
235 erase RNA, is further hypermethylated at the exocyclic N2 of the guanosine to create a trimethylguano
236 trans isomers at the 9,10 positions) by the exocyclic N2-amino group of O6-allyl-3',5'-di-O-(tert-bu
237 In contrast, the unmethylated cytosine's exocyclic N4 amino group (NH2) and its ring carbon C5 at
238 s binding of the C5 base takes place via the exocyclic N4 site, resulting in the anti-cytosine rotame
239 methylation by Erm methyltransferases of the exocyclic N6 of A2058 (E. coli numbering) that forms the
241 ic NH group at the 4-position, as well as an exocyclic NH group linked to the 3-position of the benzo
242 e-dependent concerted frequency shifts of dA exocyclic NH(2) and dT C4=O vibrational modes suggest th
243 nd allows the complementary synthesis of the exocyclic nitrile product shown, and we demonstrate cont
244 ate backbone as well as the ring nitrogen or exocyclic nitrogen and oxygen atoms of nucleobases.
248 akes a hydrogen-bonding interaction with the exocyclic nitrogen of the adenine ring, had minimal effe
251 obtained by hydrogenation of the C(4')-C(5') exocyclic olefin has been shown to be (R) at the C(4') n
256 l hydrogen atoms on each cage with the empty exocyclic orbitals on B12 of the other cage was found.
258 res highlight the critical importance of the exocyclic oxygen's interaction with the invariant argini
259 for removing promutagenic alkyl lesions from exocyclic oxygens located in the major groove of DNA, i.
260 e-determining step, involves breaking of the exocyclic P-O bond where a metal-ligated water molecule
261 We have developed biologically active small exocyclic peptide mimetics that disable apoptotic functi
262 In the two cAMP-binding sites of RIalpha, exocyclic phosphate oxygens of cAMP were identified to m
264 endence of the potency on a basic (Arg, Lys) exocyclic residue that addressed the S1' binding pocket,
265 double bond to a single bond in the 5-member exocyclic ring and are formed by chloroethyl nitrosourea
266 , these products compete with intramolecular exocyclic ring formation by meso-phenyl ring addition, w
270 erved for the free-base derivative, with the exocyclic ring-containing dimerization product isolated
271 re stable tert-butyl alcohol, intramolecular exocyclic ring-quenching is observed in 51% yield with n
273 conjugation between the sigma orbital of the exocyclic Si-C bond and the pi orbital of the oligoaryle
274 e allene unit, while the (Z)-geometry of the exocyclic stannylvinylidene is a consequence of the syn-
276 esponding interaction of the electronegative exocyclic substituent with O5 (exo-anomeric effect).
277 sted of a benzimidazole ring with one or two exocyclic substituent(s) that are either electron-donati
279 The compounds vary in the size of their exocyclic substituents, which range from hydrogen to iod
281 tRNA2(Gln) transcripts demonstrates that the exocyclic sulfur moiety improves tRNA binding affinity t
283 Ps consist of a thiolactone macrocyle and an exocyclic "tail", both of which are important for functi
286 dditionally, this transformation produces an exocyclic, tetrasubstituted alkene through which the bic
291 imple methylene group (i.e., a homologue) or exocyclic unsaturation between the thiazolidine ring and
292 otonation followed by desilylation generates exocyclic unstabilized ylides that undergo cycloaddition
293 is formed by only three amino acids, with an exocyclic ureido phenylalanine moiety at its C-terminus.
295 microbe-specific glycans, indicated that the exocyclic vicinal diol coordinates to a protein-bound ca
299 he order of O > NH congruent with S, whereas exocyclic (Y) substituents increase it in the order of C
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