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Selenium and Tellurium Derivatives of Carbohydrates and Nucleotides

Organic Selenium and Tellurium (2013)

  1. Anna Maciaszek,
  2. Agnieszka Tomaszewska,
  3. Piotr Guga

Published Online: 28 APR 2014

DOI: 10.1002/9780470682531.pat0722

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Maciaszek, A., Tomaszewska, A. and Guga, P. 2014. Selenium and Tellurium Derivatives of Carbohydrates and Nucleotides. Patai's Chemistry of Functional Groups. 1–42.

Author Information

  1. Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Bioorganic Chemistry, Poland

Publication History

  1. Published Online: 28 APR 2014

Chemistry Terms

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Abstract

Sugars, nucleosides, nucleotides and oligonucleotides labeled with a selenium atom in a sugar moiety, in a heterocyclic base, or within an internucleotide bond are synthesized, mostly, as analogs of naturally occurring biomolecules to be used in structural studies by means of X-ray crystallography. Typically, selenium is substituted for an oxygen atom already present in the parent molecule, but labeling in non-oxygen centers is also possible. Although in the synthesis of nucleosides introducing the chalcogen label can be done at any stage (i.e. before or after the glycosidic bond is formed), methods for conversion of natural nucleosides into the seleno derivatives are very useful, and are further used for synthesis of monomers suitable for synthesis of labeled oligonucleotides on a solid support. Interestingly, many types of selenium-labeled oligonucleotides can form with DNA or RNA templates the higher order structures (e.g. duplexes, triplexes) of thermodynamic stability comparable to those formed by unmodified oligomers. Similar research, although less intense, is carried on with tellurium-labeled biomolecules. The electronic and atomic properties of tellurium make this element excellent for labeling of biomolecules for X-ray analysis. Unfortunately, strong metallic properties of tellurium result in weak covalent bonds with carbon and hydrogen. As a result, the telluro derivatives are much less stable compared to seleno compounds, and their purification and usage is more arduous.

Keywords:

  • selenosugars;
  • selenosugars;
  • tellurosugars;
  • Se-DNA;
  • Se-RNA;
  • Te-DNA;
  • PSe-DNA

Featured Compounds

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  1. 1 - 117
Compound 15
Molecular Weight:759.8461
Molecular Formula:C43H45N5O8
InChIKey:FLJTYNOHIRNRCR-UQDPWRLZSA-N
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Compound 73
Molecular Weight:758.66
Molecular Formula:C40H40O5Se2
InChIKey:KWNJTORWCLHSBU-PHAUOLPESA-N
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Compound 46
Molecular Weight:932.9
Molecular Formula:C45H56N7O8PSe
InChIKey:NWOHFKQVVLFWPR-RXFNQRAYSA-N
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Compound 82
Molecular Weight:209.1
Molecular Formula:C6H10O3Se
InChIKey:HFABTHPMUHEXJY-ZXXMMSQZSA-N
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Compound 86a
Molecular Weight:361.33
Molecular Formula:C12H18N2O4SeSi
InChIKey:XCMXMSJBOPVGRI-ZCZLBPHLSA-N
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Compound 87
Molecular Weight:341.25
Molecular Formula:C18H15PSe
InChIKey:ZFVJLNKVUKIPPI-UHFFFAOYSA-N
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Compound 94
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 54
Molecular Weight:491.55
Molecular Formula:C24H32O4SeSi
InChIKey:KTHLGIMCZTVWQE-DBJIZHOSSA-N
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Compound 91b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 97
Molecular Weight:917.8
Molecular Formula:C28H38O18Te2
InChIKey:XRJHRSGLGYZBJS-AXXYRMHMSA-N
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Compound 98
Molecular Weight:502
Molecular Formula:C17H26O9Te
InChIKey:HATUSUINUFDTCX-UUAJXVIYSA-N
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Compound 48
Molecular Weight:727.898
Molecular Formula:C27H44F3N5O9SSi2
InChIKey:QZCDVIAPCPENKE-MASGSYHESA-N
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Compound 83
Molecular Weight:288.06
Molecular Formula:C6H10O3Se2
InChIKey:QEIFFBHHOUKBTC-ZXXMMSQZSA-N
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Compound 84
Molecular Weight:209.1
Molecular Formula:C6H10O3Se
InChIKey:FSIRIXFPHWDKSR-ZXXMMSQZSA-N
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Compound 66
Molecular Weight:425.33
Molecular Formula:C16H26O8Se
InChIKey:QKITWWILOOZAQK-AZLQIUJGSA-N
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Compound 69
Molecular Weight:357.26
Molecular Formula:C15H18O5Se
InChIKey:CUOOQHOIIFOARB-GFQSEFKGSA-N
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Compound 52c
Molecular Weight:569.11
Molecular Formula:C11H17N2O14P3Se
InChIKey:BKZMSYVDZGLPSC-SZVQBCOZSA-J
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Compound 41
Molecular Weight:888.85
Molecular Formula:C43H52N7O7PSe
InChIKey:GNHHKBNWRRKVJH-PGHUPTSKSA-N
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Compound 8
Molecular Weight:860.84
Molecular Formula:C43H52N5O7PSe
InChIKey:JWWZHJJINIJXTE-GFZSHSHLSA-N
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Compound 3
Molecular Weight:199.07
Molecular Formula:C5H4N4Se
InChIKey:NGMMEPMKKHBFDS-UHFFFAOYSA-N
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Compound 61
Molecular Weight:554.7911
Molecular Formula:C35H42O4Si
InChIKey:CEAJAKDDRMDYRF-NOCHOARKSA-N
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Compound 53
Molecular Weight:178.14
Molecular Formula:C6H10O6
InChIKey:SXZYCXMUPBBULW-MMJIIOHLSA-N
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Compound 47
Molecular Weight:595.8358
Molecular Formula:C26H45N5O7Si2
InChIKey:RYRMXMSXLHPLAT-AFPVUDKHSA-N
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Compound 105
Molecular Weight:734.3
Molecular Formula:C36H34N2O7Te
InChIKey:XNNVEOHTDYYRSQ-RKKDRKJOSA-N
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Compound 33
Molecular Weight:258.228
Molecular Formula:C10H14N2O6
InChIKey:DWRXFEITVBNRMK-JXOAFFINSA-N
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Compound 50
Molecular Weight:430.32
Molecular Formula:C15H21N5O5Se
InChIKey:JFURNSDFUGJNOX-AKAIJSEGSA-N
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Compound 12
Molecular Weight:607.56
Molecular Formula:C31H32N2O6Se
InChIKey:DLJDVDIBJLZOKA-UPRLRBBYSA-N
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Compound 99
Molecular Weight:516.1
Molecular Formula:C26H28O3Te
InChIKey:RNMIXZGJVPPQBA-JWQCQUIFSA-N
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Compound 44
Molecular Weight:793.92
Molecular Formula:C33H50N6O8SeSi2
InChIKey:ZDQRLYRSVZCZJL-DWCTZGTLSA-N
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Compound 29
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 86b
Molecular Weight:375.35
Molecular Formula:C13H20N2O4SeSi
InChIKey:NCAZUAWFWULZIQ-GHXJOQNMSA-N
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Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 34
Molecular Weight:542.5791
Molecular Formula:C31H30N2O7
InChIKey:BQEQCEZNLIKSSH-CITHKVLSSA-N
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Compound 92
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2a
Molecular Weight:138.097
Molecular Formula:C5H7NaO3
InChIKey:KYNWPSPTEJCKDO-UHFFFAOYSA-N
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Compound 7
Molecular Weight:660.62
Molecular Formula:C34H35N3O6Se
InChIKey:CYUJRKAEVMPDOD-OJDZSJEKSA-N
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Compound 10
Molecular Weight:560.661
Molecular Formula:C31H32N2O6S
InChIKey:AMTYSYZKQRHTLI-UPRLRBBYSA-N
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Compound 72
Molecular Weight:467.46
Molecular Formula:C26H28O3Se
InChIKey:OLWYOLJABSUCTJ-JWQCQUIFSA-N
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Compound 88
Molecular Weight:215.13
Molecular Formula:C7H4OSSe
InChIKey:FRHLUUZBXZZXSL-UHFFFAOYSA-N
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Compound 93
Molecular Weight:541.1
Molecular Formula:C10H17N2O13P3Se
InChIKey:MRVQVZDKOIYNHF-MXWQNOQOSA-J
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Compound 104
Molecular Weight:848.5
Molecular Formula:C42H48N2O7SiTe
InChIKey:OZQIXMHOVFKQTQ-QOZRZDGHSA-N
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Compound 95
Molecular Weight:608
Molecular Formula:C19H29O12PTe
InChIKey:HKRIQTVSHWRERC-SFFUCWETSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:1076.09
Molecular Formula:C55H65N8O8PSe
InChIKey:OKKMVEDVOJAIND-USGPYGQNSA-N
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Compound 14
Molecular Weight:860.84
Molecular Formula:C43H52N5O7PSe
InChIKey:XWFHWIWPVQWVLM-GFZSHSHLSA-N
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Compound 11
Molecular Weight:574.687
Molecular Formula:C32H34N2O6S
InChIKey:MOXKIFKFPICGDJ-ZGIBFIJWSA-N
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Compound 91a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 71
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 78
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 85
Molecular Weight:281.28
Molecular Formula:C9H18O3SeSi
InChIKey:FZTIYFNUWVWIBQ-HXFLIBJXSA-N
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Compound 68
Molecular Weight:279.19
Molecular Formula:C10H16O4Se
InChIKey:GSWMKJNWHAXRDT-BZNPZCIMSA-N
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Compound 21
Molecular Weight:407.16
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 77
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60
Molecular Weight:316.3915
Molecular Formula:C19H24O4
InChIKey:ZHZUBMCDANCCBT-MOPGFXCFSA-N
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Compound 42
Molecular Weight:283.2407
Molecular Formula:C10H13N5O5
InChIKey:NYHBQMYGNKIUIF-FJFJXFQQSA-N
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Compound 35
Molecular Weight:798.011
Molecular Formula:C43H55N5O8Si
InChIKey:GRKOTVLBBPNAHU-CISTVLBBSA-N
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Compound 37
Molecular Weight:798.011
Molecular Formula:C43H55N5O8Si
InChIKey:GRKOTVLBBPNAHU-GJHGNUNFSA-N
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Compound 52a
Molecular Weight:333.2
Molecular Formula:C11H14N2O5Se
InChIKey:ZKHVXTAORHJMFP-SZVQBCOZSA-N
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Compound 62
Molecular Weight:361.34
Molecular Formula:C19H22O2Se
InChIKey:ATJJUPRBLSHZMZ-RBUKOAKNSA-N
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Compound 51
Molecular Weight:580.14
Molecular Formula:C11H18N5O12P3Se
InChIKey:ADBAQDSQHYIZKY-IOSLPCCCSA-J
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Compound 45
Molecular Weight:904.85
Molecular Formula:C43H52N7O8PSe
InChIKey:BJHMVQXYCNAJPG-QTFHQJRDSA-N
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Compound 67
Molecular Weight:277.18
Molecular Formula:C10H14O4Se
InChIKey:NPJCXFYJCYUZQM-BZNPZCIMSA-N
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Compound 31
Molecular Weight:623.55
Molecular Formula:C31H32N2O7Se
InChIKey:MBAPSRZJRARBGE-YXINZVNLSA-N
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Compound 80
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:JUSRGBNWFOHRCD-KAZBKCHUSA-N
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Compound 5
Molecular Weight:544.595
Molecular Formula:C31H32N2O7
InChIKey:UBTJZUKVKGZHAD-UPRLRBBYSA-N
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Compound 101
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 79
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 52
Molecular Weight:596.14
Molecular Formula:C11H18N5O13P3Se
InChIKey:KAZQMFMUZDYQRH-KQYNXXCUSA-J
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Compound 36
Molecular Weight:930.073
Molecular Formula:C44H54F3N5O10SSi
InChIKey:GROJHOZNIOLHJT-CISTVLBBSA-N
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Compound 38
Molecular Weight:930.073
Molecular Formula:C44H54F3N5O10SSi
InChIKey:GROJHOZNIOLHJT-JCTMMKHWSA-N
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Compound 49
Molecular Weight:672.82
Molecular Formula:C27H47N5O6SeSi2
InChIKey:HOTJJUIBGLBZJI-RKCWLVDCSA-N
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Compound 20
Molecular Weight:823.77
Molecular Formula:C40H49N4O8PSe
InChIKey:VXQAQLQJSZGZDM-NYPUCURUSA-N
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Compound 22
Molecular Weight:351.1178
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 81
Molecular Weight:224.232
Molecular Formula:C7H12O6S
InChIKey:XKZCFVSRKXGUET-GBNDHIKLSA-N
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Compound 4
Molecular Weight:213.1
Molecular Formula:C6H6N4Se
InChIKey:ZEKMVARREOZNBN-UHFFFAOYSA-N
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Compound 90
Molecular Weight:279.15
Molecular Formula:C11H8N2O2Se
InChIKey:JHHVXHKIVRZANT-UHFFFAOYSA-N
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Compound 34
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 56
Molecular Weight:584.64
Molecular Formula:C28H35N3O4SeSi
InChIKey:BUIONWHDVATXOA-WJNCPCKPSA-N
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Compound 58
Molecular Weight:351.42
Molecular Formula:C14H28O3SeSi
InChIKey:CUVLYGUOOFWPBS-TUAOUCFPSA-N
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Compound 91c
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 65
Molecular Weight:504.29
Molecular Formula:C16H26O8Se2
InChIKey:KWBVTDDWHPKXAE-AZLQIUJGSA-N
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Compound 1b
Molecular Weight:189.07
Molecular Formula:C5H6N2OSe
InChIKey:KVBVUHYWSKATJH-UHFFFAOYSA-N
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Compound 52b
Molecular Weight:835.78
Molecular Formula:C41H49N4O8PSe
InChIKey:PVGOZGVSTVCPRG-SWEAJAEYSA-N
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Compound 2b
Molecular Weight:152.1236
Molecular Formula:C6H9NaO3
InChIKey:XUEFRTJZRULQFN-UHFFFAOYSA-N
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43
Molecular Weight:848.991
Molecular Formula:C33H47F3N6O11SSi2
InChIKey:JDTRYOGJJHNPFV-IIHCQYLKSA-N
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Compound 39
Molecular Weight:875
Molecular Formula:C44H57N5O7SeSi
InChIKey:RCOBADGWOFFHCG-KEJRJOSKSA-N
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Compound 18
Molecular Weight:436.4141
Molecular Formula:C23H20N2O7
InChIKey:WTTRUBICDWFROZ-NLWGTHIKSA-N
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Compound 26
Molecular Weight:242.2286
Molecular Formula:C10H14N2O5
InChIKey:IQFYYKKMVGJFEH-XLPZGREQSA-N
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Compound 76a
Molecular Weight:483.46
Molecular Formula:C26H28O4Se
InChIKey:RRTOLEHAULSGBX-NITSXXPLSA-N
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Compound 76b
Molecular Weight:483.46
Molecular Formula:C26H28O4Se
InChIKey:RRTOLEHAULSGBX-SIDNZMCZSA-N
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Compound 19
Molecular Weight:529.4
Molecular Formula:C24H22N2O7Se
InChIKey:BWZTYGSALGQUNO-NLWGTHIKSA-N
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Compound 64
Molecular Weight:344.38
Molecular Formula:C15H20O7S
InChIKey:RMWKMMUSFZVFMX-XJFOESAGSA-N
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Compound 102
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:660.62
Molecular Formula:C34H35N3O6Se
InChIKey:YBCVYIFAWHOLKH-OJDZSJEKSA-N
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Compound 40
Molecular Weight:688.63
Molecular Formula:C34H35N5O6Se
InChIKey:NTSRZGLDIOVSMQ-JHZZHVAFSA-N
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 6
Molecular Weight:667.8261
Molecular Formula:C36H41N5O6Si
InChIKey:WSSMPUJEKHZYFD-WIHCDAFUSA-N
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Compound 63
Molecular Weight:329.21
Molecular Formula:C13H14O5Se
InChIKey:USCJSTJPSUDOLT-KIYNQFGBSA-N
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Compound 28
Molecular Weight:558.47
Molecular Formula:C22H34N5O5PSe
InChIKey:ZVGBYLJETQWBBD-LAHROCKRSA-N
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Compound 103
Molecular Weight:418.4816
Molecular Formula:C26H26O5
InChIKey:HNNDUTQOVDOIQA-LOSJGSFVSA-N
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Compound 57
Molecular Weight:148.114
Molecular Formula:C5H8O5
InChIKey:CUOKHACJLGPRHD-BXXZVTAOSA-N
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Compound 23
Molecular Weight:631.37
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:258.294
Molecular Formula:C10H14N2O4S
InChIKey:PISWNSOQFZRVJK-XLPZGREQSA-N
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Compound 30
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 100
Molecular Weight:675.9
Molecular Formula:C26H28Br2O3Te
InChIKey:ZMNRZCZDQBRAME-JWQCQUIFSA-N
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Compound 75
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16
Molecular Weight:875.87
Molecular Formula:C46H48N6O7Se
InChIKey:ZSVQJXGCKAICIK-PQTOBSADSA-N
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Compound 59
Molecular Weight:328.4022
Molecular Formula:C20H24O4
InChIKey:MVQADNLPVMKXPL-ABZYKWASSA-N
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Compound 27
Molecular Weight:358.25
Molecular Formula:C13H17N3O4Se
InChIKey:KODBLEBVJLSRNA-HBNTYKKESA-N
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Compound 89
Molecular Weight:520.35
Molecular Formula:C12H28O4P2S2Se2
InChIKey:NDLCNQLVKBQRNV-UHFFFAOYSA-N
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Compound 1a
Molecular Weight:175.05
Molecular Formula:C4H4N2OSe
InChIKey:NGXVPIDNNNKQIL-UHFFFAOYSA-N
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Compound 86
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 32
Molecular Weight:823.77
Molecular Formula:C40H49N4O8PSe
InChIKey:PCVXMAONSDESOC-HENUTREFSA-N
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Compound 55
Molecular Weight:585.63
Molecular Formula:C28H34N2O5SeSi
InChIKey:FGNJWYCMZSOPBA-WJNCPCKPSA-N
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Compound 70
Molecular Weight:438.42
Molecular Formula:C18H33NO6Se
InChIKey:ZQUWJHALXGWLJQ-UXXRCYHCSA-N
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Compound 74
Molecular Weight:573.58
Molecular Formula:C33H34O4Se
InChIKey:AHTFQPTWGRDCEI-XIWRNSNHSA-N
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