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2 and the lack of cross-link formation by the exocyclic 1,N(2)-dG adduct of (6R,8S,11R) stereochemistr
3 ccordingly, the chemistry of the HNE-derived exocyclic 1,N(2)-dG adduct of (6S,8R,11S) stereochemistr
4 rmation of the interstrand cross-link by the exocyclic 1,N(2)-dG adduct of (6S,8R,11S) stereochemistr
6 acrolein- and the 6R-crotonaldehyde-derived exocyclic 1,N(2)-dG adducts form interstrand N(2)-dG:N(2
8 ponding acrolein- and crotonaldehyde-derived exocyclic 1,N(2)-dG adducts undergo ring-opening to N(2)
11 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
21 ethyl)-3,N(4)-etheno-C (8-HM-epsilonC) is an exocyclic adduct resulting from the reaction of dC with
23 stress that reacts with guanine to form the exocyclic adduct, pyrimido[1,2- alpha]purin-10(3H)-one (
25 n DNA lesions and the enzyme, the effects of exocyclic adducts on DNA cleavage mediated by human topo
26 Together, these data suggest that multiple exocyclic adducts undergo oxidation and glycolytic cleav
30 reaction are methylenecyclopentenes, and the exocyclic alkene is generally obtained with high Z selec
31 e RT dNTP binding site that accommodates the exocyclic alkene moiety of ETV was predicted, establishi
32 ated with alkene transposition to afford the exocyclic alkene; alternatively, the reactivity of the c
33 he 3,3-difluoro-2,4-dione intermediates gave exocyclic alkenes that underwent hydrogenation accompani
34 losing metathesis to afford the synthesis of exocyclic allylic amines from their endocyclic precursor
35 ment with allylic transposition yielding the exocyclic allylsilane 3a with excellent diastereoselecti
36 ray crystal structure of DHO showed that the exocyclic alpha-carboxylate of dihydroorotate is bound t
37 region in the resulting product contains an exocyclic amide positioned alpha to the peptide backbone
38 sely, adding the equivalent of adenine's C-6 exocyclic amine (N-6) to 1- and 3-deazapurines also enha
40 e local DNA environment and proximity of the exocyclic amine determine the selectivity for reaction w
41 o metabolic activation by N-oxidation of the exocyclic amine group to produce N-hydroxylated metaboli
42 h bioactivate HAAs by N-hydroxylation of the exocyclic amine group; the resultant N-hydroxy-HAA metab
43 terification rate, implying that the guanine exocyclic amine is not a critical determinant of DNA cle
44 a combination of hydrogen bonding to the N6 exocyclic amine of adenosine and steric exclusion of the
45 A pair is in an imino conformation where the exocyclic amine of G contributes approximately 1.4 kcal/
46 ronment and provided a rationale for how the exocyclic amine of nucleobase 8 promotes productive, in-
48 th steps; moreover, proton transfer from the exocyclic amine of protonated C75 to the nonbridging oxy
49 drogen bond between the formyl group and the exocyclic amine of the 3'-neighbor adenine stabilizes th
50 en bonding between the formyl oxygen and the exocyclic amine of the 3'-neighboring adenine stabilizin
51 esence of a unique hydrogen bond between the exocyclic amine of the inhibitor and threonine 106 which
52 phospholane approach, which does not require exocyclic amine protection of the nucleobase, has been s
53 through hydrogen bond formation between the exocyclic amine protons of G(7) and the (iPr)Th nitrogen
54 denosine receptor (A3AR) agonists lacking an exocyclic amine resulted from an unexpected reaction dur
57 can partially compensate for the lack of an exocyclic amine, an otherwise important contributor to r
60 m correlation (NOESY-HSQC) NMR, in which the exocyclic amines at X(7) or Y(19) were (15)N-labeled.
64 hat binds the AIP thiolactone ring while the exocyclic amino acid tail interacts with loop 1 to facil
65 the determination of the contribution of the exocyclic amino group "N2" of the guanine base to nucleo
66 no selective, total syntheses of the stable exocyclic amino group adducts formed by the single-elect
69 Evidently, tertiary interactions with the exocyclic amino group of a G in a single G.A pair can in
70 observed a distance between fluorine and the exocyclic amino group of A that is consistent with a H-b
73 which supports that the deprotonation at the exocyclic amino group of cytosine cation radical is esse
75 tral G clearly shows the crucial role of the exocyclic amino group of G in sequence-specific recognit
76 )-anti-benzo[a]pyrene diol epoxide, with the exocyclic amino group of guanine ((+)-trans-anti-[BP]-N(
78 ne diol epoxide, which can attack DNA at the exocyclic amino group of guanine to form the major (+)-t
81 etermined that the hydrogen bond between the exocyclic amino group of guanosine and the 2'-hydroxyl g
82 o probe the putative interaction between the exocyclic amino group of the guanosine nucleophile and t
83 nd DNA-DNA cross-links via reaction with the exocyclic amino group on a nearby 2-deoxyguanosine or 2-
84 try analysis revealed that Scabin labels the exocyclic amino group on guanine bases in either single-
91 introduced by means of a ring closure of the exocyclic amino groups of a pyrimidinone using [13C]sodi
93 ntaining intrastrand cross-links between the exocyclic amino groups of adjacent deoxyguanosines has b
95 in antagonist CGS15943 1 overlapped, and the exocyclic amino groups of each were H-bonded to the side
96 distortions of the DNA duplexes, because the exocyclic amino groups of flanking guanines on both stra
97 ronmental carcinogen benzo[a]pyrene), to the exocyclic amino groups of guanine or adenine in oligonuc
98 zo[a]pyre ne {B[a]P DE-2 (2)} at C-10 by the exocyclic amino groups of protected purine nucleosides i
100 sented here show that M(1)dG and its stable, exocyclic analog 1,N(2)-propanodeoxyguanine (PdG), arres
103 tailed investigation of the influence of the exocyclic base adduct on the overall helical structure a
104 ed the possibility that structurally similar exocyclic base adducts may be good candidates for enzyma
105 as permits prediction of conformation of the exocyclic bond by comparison with the known solution (=
107 basis of this model the conformation of the exocyclic bond in ring I of 6'-homologated 4,5-disubstit
108 oted more ozone reactions with the remaining exocyclic bond of oxidized limonene products in the SOA
109 ith a view to facilitating prediction of the exocyclic bond to the pyranoside ring in higher carbon s
112 in the prediction of the conformation of the exocyclic bonds in other 2-(1-hydroxyalkyl)-3-hydroxytet
114 nal monomer, contains both a highly reactive exocyclic C horizontal lineC bond and a highly stable fi
115 e E or E,E configuration with respect to the exocyclic C horizontal lineC bond is stabilized by inter
116 etween the electron donor groups (oxygen and exocyclic C horizontal lineC double bond) and CH bonds o
117 ose predictable conformational biases on the exocyclic C-5-C-6 bond, as determined by (1)H-(1)H and (
119 tributed to a rotation around one of the two exocyclic C-C bonds bridging phenol and imidazolinone gr
121 sugars for the most part) suggests that the exocyclic C-O bond in acetate esters of cyclic alcohols
123 r-catalyzed addition of ZnEt2 (ZnBu2) to the exocyclic C=C bond of pentafulvenes C5H4(=CHAr) (Ar=2-Me
124 possess Z-stereochemistry with regard to the exocyclic C=C double bond at the 2-position of the ring.
126 ) with 2'-deoxyinosine (dI), which lacks the exocyclic C2 amino group present in dG, also prevented D
128 of NAD(P)H is transferred to the unsaturated exocyclic C6 carbon of HMMF, resulting in a cyclic achir
131 rization to occur, while substitution at the exocyclic carbon atom has an impact on the reaction path
133 dding electron-withdrawing CF3 groups to the exocyclic carbon of this meta-disubstituted benzyl catio
134 Substitution of both oxygen atoms in the exocyclic carbonyl groups of the thymine chromophore by
135 Core characteristics of the series are an exocyclic carbonyl moiety as a hydrogen bond acceptor an
136 to utilize multiple J-couplings sensitive to exocyclic CH(2)OH conformation, the ensemble of experime
137 ulfide bond were observed in addition to the exocyclic cleavages typically seen from CID of [M + nH](
138 2 dihedral, and a greater sampling of non-TG exocyclic conformations, particularly the GG conformatio
142 ns suggest that substituents proximal to the exocyclic COOH group (i.e., the C4-O4 bond) influence th
144 accessible through dipolar cycloadditions of exocyclic cyclohexenones and provides a fundamentally ne
145 rates a mixture of 3E- and 3Z-olefins of the exocyclic-Delta(3),Delta(5)-dihydrohydroxyphenylpyruvate
146 uted cyanoolefins BTF and TCNE to add to the exocyclic diene portion of 1-isopropenyl-1,3-cyclopentad
147 ient of 0.5, these results indicate that the exocyclic dienolate is 3.0 kcal/mol more stable than its
148 pair by Escherichia coli AlkB dioxygenase of exocyclic DNA adducts 3,N(4)-ethenocytosine, 1,N(6)-ethe
150 thenoguanine (N(2),3-epsilonG) is one of the exocyclic DNA adducts produced by endogenous processes (
152 mary, our data suggest that acrolein-induced exocyclic DNA lesions can be bypassed by mitochondrial D
155 tructurally different N-heterocycles with an exocyclic double bond (= N-heterocyclic olefins, NHOs) h
159 re made by dihalocarbene addition across the exocyclic double bond of readily accessible 3-alkylidene
160 n addition, gem-dimethyl substitution on the exocyclic double bond of the 2-methyleneaziridine is tol
161 nduced enzyme catalyzes the reduction of the exocyclic double bond of the highly reactive precursor 4
162 in, respectively, also reduce the more inert exocyclic double bond of the same 4-substituted Delta1-p
164 e concern around potential reactivity of the exocyclic double bond present in series I toward nucleop
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
197 s between the equivalent of both N-1 and the exocyclic group at C-6 of a purine NTP (2-fluoroadenine,
198 rate puckering conformations and the role of exocyclic groups have not yet been thoroughly addressed.
200 losing base pair showed that the presence of exocyclic groups in the major groove of purines 3' to th
203 ructure and to evaluate the influence of the exocyclic groups, Density Functional Theory (DFT) calcul
207 mation of another product with an additional exocyclic hemiaminal group formed by reaction with the c
209 ramolecular interactions between consecutive exocyclic hydroxyl groups, which are stable in nonpolar
210 on and nearby protons and carbons within the exocyclic hydroxymethyl group (CH(2)OH) of each compound
213 the resulting product further oxidizes to an exocyclic iminium ion (by the perferryl-oxygen complex);
217 eske aromatic oxygenases, DMO oxygenates the exocyclic methyl group, rather than the aromatic ring, o
219 al and carboxylic acid analogs containing an exocyclic methylene instead of an epoxide, indicating th
221 clusive formation of tricycles possessing an exocyclic methylene moiety, whereas base-mediated condit
225 from the carbene carbon atom to the attached exocyclic moiety, and low-valent and low-coordinate addu
226 ske non-heme iron oxygenase that performs an exocyclic monooxygenation, incorporating O(2) into a sid
227 ter metabolic activation, can react with the exocyclic N (2) amino group of guanine to generate four
228 Further support for the importance of the exocyclic N(2)-amino group in this reaction was provided
230 mutagenicity of trans-opened adducts at the exocyclic N(2)-amino group of guanine by the (+)-(7R,8S,
236 group substitution at G33 indicates that its exocyclic N2 interacts directly with the scissile phosph
237 erase RNA, is further hypermethylated at the exocyclic N2 of the guanosine to create a trimethylguano
238 trans isomers at the 9,10 positions) by the exocyclic N2-amino group of O6-allyl-3',5'-di-O-(tert-bu
239 In contrast, the unmethylated cytosine's exocyclic N4 amino group (NH2) and its ring carbon C5 at
240 s binding of the C5 base takes place via the exocyclic N4 site, resulting in the anti-cytosine rotame
241 methylation by Erm methyltransferases of the exocyclic N6 of A2058 (E. coli numbering) that forms the
243 ic NH group at the 4-position, as well as an exocyclic NH group linked to the 3-position of the benzo
244 nd allows the complementary synthesis of the exocyclic nitrile product shown, and we demonstrate cont
245 ate backbone as well as the ring nitrogen or exocyclic nitrogen and oxygen atoms of nucleobases.
249 akes a hydrogen-bonding interaction with the exocyclic nitrogen of the adenine ring, had minimal effe
252 lized [3.3.1]-bridged bicycles along with an exocyclic olefin and an all-carbon quaternary stereocent
258 l hydrogen atoms on each cage with the empty exocyclic orbitals on B12 of the other cage was found.
259 res highlight the critical importance of the exocyclic oxygen's interaction with the invariant argini
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.
294 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