Hydrogen Peroxide Oxidation of Phosphite Triesters in Oligonucleotide Syntheses

The oxidation of P(III) phosphite triesters to stable P(V) phosphates in oligonucleotide syntheses using hydrogen peroxide was demonstrated in neutral aqueous acetonitrile as a cheap, green alternative to the widely used iodine pyridine procedure. This oxidation was utilized on short oligomers of tw...

Full description

Saved in:
Bibliographic Details
Published inOrganic process research & development Vol. 14; no. 1; pp. 295 - 297
Main Author Cvetovich, Raymond J
Format Journal Article
LanguageEnglish
Published American Chemical Society 15.01.2010
Online AccessGet full text

Cover

Loading…
Abstract The oxidation of P(III) phosphite triesters to stable P(V) phosphates in oligonucleotide syntheses using hydrogen peroxide was demonstrated in neutral aqueous acetonitrile as a cheap, green alternative to the widely used iodine pyridine procedure. This oxidation was utilized on short oligomers of two nucleosides.
AbstractList The oxidation of P(III) phosphite triesters to stable P(V) phosphates in oligonucleotide syntheses using hydrogen peroxide was demonstrated in neutral aqueous acetonitrile as a cheap, green alternative to the widely used iodine pyridine procedure. This oxidation was utilized on short oligomers of two nucleosides.
Author Cvetovich, Raymond J
Author_xml – sequence: 1
  givenname: Raymond J
  surname: Cvetovich
  fullname: Cvetovich, Raymond J
  email: rcvetovich@gmail.com
BookMark eNptkEFLAzEQhYNUsK0e_Ae5ePCwmuxu0uQoRVuhsAUreFvSZNJNqUlJtmD99aZUPHmZN4fvDfPeCA188IDQLSUPlJT0MewlIaSuvy_QkLKSFEzwj0HeiagKTjm5QqOUtplhnJZD1MyPJoYNeLyEGL6cAdzkqXoXPA4WL7uQ9p3rAa-ig9RDTNh53OzcJviD3kHoT563o-87SJCu0aVVuwQ3vzpG7y_Pq-m8WDSz1-nTolAlk32hlaktEBBryoSeTKqJUVrUxhANVhirQSpSZUCuLbcSjBGWSyYZz-E00dUY3Z_v6hhSimDbfXSfKh5bStpTE-1fE5m9O7NKp3YbDtHnz_7hfgCkomGq
CitedBy_id crossref_primary_10_1021_acs_oprd_9b00462
crossref_primary_10_1002_ejoc_201300864
Cites_doi 10.1016/j.tetlet.2006.10.016
10.1039/b404932m
10.1038/nmeth911
10.1073/pnas.0306111101
10.1016/S0960-894X(03)00754-6
10.1021/ol000364w
10.1021/ol9910518
10.1038/sj.gt.3302703
10.1016/S0040-4039(00)84946-1
10.1016/S0040-4039(00)98437-5
10.1016/S0040-4020(01)87958-8
10.1021/ja030376n
ContentType Journal Article
Copyright Copyright © 2009 American Chemical Society
Copyright_xml – notice: Copyright © 2009 American Chemical Society
DBID AAYXX
CITATION
DOI 10.1021/op900044z
DatabaseName CrossRef
DatabaseTitle CrossRef
DatabaseTitleList
DeliveryMethod fulltext_linktorsrc
Discipline Engineering
Chemistry
EISSN 1520-586X
EndPage 297
ExternalDocumentID 10_1021_op900044z
a977035791
GroupedDBID 123
4.4
55A
5VS
7~N
AABXI
ABMVS
ABUCX
ACGFS
ACS
AEESW
AENEX
AFEFF
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
BAANH
CS3
DU5
EBS
ED
ED~
EJD
F5P
GNL
IH9
JG
JG~
LG6
RNS
ROL
UI2
VF5
VG9
W1F
X
XKZ
-~X
AAYXX
ABJNI
ABQRX
ADHLV
AHGAQ
CITATION
CUPRZ
GGK
ID FETCH-LOGICAL-a259t-cad4fe0e8b158c7737dac84dd0cef8dfce9a03e0e9bf6f9edd8f695956004c0c3
IEDL.DBID ACS
ISSN 1083-6160
IngestDate Fri Dec 06 05:36:37 EST 2024
Thu Aug 27 13:43:21 EDT 2020
IsPeerReviewed true
IsScholarly true
Issue 1
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-a259t-cad4fe0e8b158c7737dac84dd0cef8dfce9a03e0e9bf6f9edd8f695956004c0c3
PageCount 3
ParticipantIDs crossref_primary_10_1021_op900044z
acs_journals_10_1021_op900044z
ProviderPackageCode JG~
55A
AABXI
GNL
VF5
XKZ
7~N
VG9
W1F
ACS
AEESW
AFEFF
ABMVS
ABUCX
IH9
BAANH
AQSVZ
ED~
UI2
PublicationCentury 2000
PublicationDate 2010-01-15
PublicationDateYYYYMMDD 2010-01-15
PublicationDate_xml – month: 01
  year: 2010
  text: 2010-01-15
  day: 15
PublicationDecade 2010
PublicationTitle Organic process research & development
PublicationTitleAlternate Org. Process Res. Dev
PublicationYear 2010
Publisher American Chemical Society
Publisher_xml – name: American Chemical Society
References Kent O. A. (ref1/cit1c) 2004; 2
Uzagare M. C. (ref7/cit7) 2003; 13
Beaucage S. L. (ref2/cit2) 1993; 49
Hayakawa Y (ref5/cit5) 1986; 27
Sierzchala A. B. (ref6/cit6) 2003; 125
Beaucage S. L. (ref3/cit3) 2001
ref11/cit11
ref12/cit12
Pei Y (ref1/cit1a) 2006; 3
Manoharan M. (ref9/cit9) 2000; 2
Gupta S. (ref1/cit1d) 2004; 101
Fourrey J.-L. (ref4/cit4) 1985; 26
Saneyoshi H. (ref10/cit10) 2006; 47
ref13/cit13
Kataoka M. (ref8/cit8) 2001; 3
Dykxhoorn D (ref1/cit1b) 2006; 13
References_xml – volume-title: Current Protocols in Nucleic Acid Chemistry
  year: 2001
  ident: ref3/cit3
  contributor:
    fullname: Beaucage S. L.
– volume: 47
  start-page: 8945
  year: 2006
  ident: ref10/cit10
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2006.10.016
  contributor:
    fullname: Saneyoshi H.
– ident: ref12/cit12
– volume: 2
  start-page: 1957
  year: 2004
  ident: ref1/cit1c
  publication-title: Org. Biomol. Chem
  doi: 10.1039/b404932m
  contributor:
    fullname: Kent O. A.
– volume: 3
  start-page: 670
  year: 2006
  ident: ref1/cit1a
  publication-title: Nature Methods
  doi: 10.1038/nmeth911
  contributor:
    fullname: Pei Y
– volume: 101
  start-page: 1927
  year: 2004
  ident: ref1/cit1d
  publication-title: Proc. Natl. Acad. Sci. U.S.A.
  doi: 10.1073/pnas.0306111101
  contributor:
    fullname: Gupta S.
– ident: ref13/cit13
– volume: 13
  start-page: 3537
  year: 2003
  ident: ref7/cit7
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/S0960-894X(03)00754-6
  contributor:
    fullname: Uzagare M. C.
– volume: 3
  start-page: 815
  year: 2001
  ident: ref8/cit8
  publication-title: Org. Lett.
  doi: 10.1021/ol000364w
  contributor:
    fullname: Kataoka M.
– volume: 2
  start-page: 243
  year: 2000
  ident: ref9/cit9
  publication-title: Org. Lett.
  doi: 10.1021/ol9910518
  contributor:
    fullname: Manoharan M.
– volume: 13
  start-page: 541
  year: 2006
  ident: ref1/cit1b
  publication-title: Gene Ther.
  doi: 10.1038/sj.gt.3302703
  contributor:
    fullname: Dykxhoorn D
– volume: 27
  start-page: 4191
  year: 1986
  ident: ref5/cit5
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)84946-1
  contributor:
    fullname: Hayakawa Y
– volume: 26
  start-page: 1217
  year: 1985
  ident: ref4/cit4
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)98437-5
  contributor:
    fullname: Fourrey J.-L.
– ident: ref11/cit11
– volume: 49
  start-page: 6123
  year: 1993
  ident: ref2/cit2
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)87958-8
  contributor:
    fullname: Beaucage S. L.
– volume: 125
  start-page: 13427
  year: 2003
  ident: ref6/cit6
  publication-title: Chem. Soc.
  doi: 10.1021/ja030376n
  contributor:
    fullname: Sierzchala A. B.
SSID ssj0005612
Score 1.9583609
Snippet The oxidation of P(III) phosphite triesters to stable P(V) phosphates in oligonucleotide syntheses using hydrogen peroxide was demonstrated in neutral aqueous...
SourceID crossref
acs
SourceType Aggregation Database
Publisher
StartPage 295
Title Hydrogen Peroxide Oxidation of Phosphite Triesters in Oligonucleotide Syntheses
URI http://dx.doi.org/10.1021/op900044z
Volume 14
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwhV1LTwIxEJ4gHtSDD9SID9Ko1yXtvns0qCEehARIuJFup1Wi2SXscoBfb5dddBOiXnrqK51pZr58068A94xpGwVFCz1bWK4nzZ1DR1u2KxxmI-VYVPm--t2R-zL2xjW4-4XBt5nBjnxNO652YNcODOzO85_O4KeOwy8pzdAxOMinG_mg6tA89Mi0EnoqMeT5CB43L3GK0pGP9iKL2nK1Lcz41_aO4bDMIclDYfQTqKm4AXudzddtDTioqAyeQq-7xHliHIX0lVl5ior0TLs2CUk06b8n6SxnE8gwx8253CaZxqT3OX1L4lzuOMnyMYNlbJLFVKVnMHp-Gna6VvmPgiUMuMksKdDViqowYl4og8AJUMjQRaRS6RC1VFxQx3TgkfY1V4ih9rmXIyfqSiqdc6jHSawugChuQp3PtReIwEWmQ6HdkEaBtAPkDlVNaJmDnpT3IJ2sKW6bTb5PqQm3GxtMZoWexnany_9muYL9gsVnFvOuoZ7NF-rGJAdZ1Fo7xxfPBrWW
link.rule.ids 314,780,784,2765,27076,27924,27925,56738,56788
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV07T8MwELZ4DMDAo4AoTwuxBtl5e0QVKEBpK7VI3SLHZ0MFSqomHcqvx05SiGCAxZNtneyz7j595-8QuqJU2cAJWODZ3HI9od8cOMqyXe5QGwiDqsq350fP7sPYG9cyOeYvjDYi1zvlJYn_rS5ANYRkJfv4sYrWPdOq0qRBneF3OYdfM5uho-GQT5YqQs2lJgKJvBGBGqHkbqfqSVQaUVaQvF3Pi-RafPzQZ_yflbtou84o8U3lAntoRaYttNFZNnJroa2G5uA-6kcLmGXabfBAagMmIHFfj-UF4UzhwWuWTw23gEcGRRvxTTxJcf998pKlRvw4K8ya4SLVqWMu8wP0fHc76kRW3VXB4hrqFJbg4CpJZJhQLxRB4ATARegCECFVCEpIxomjJ7BE-YpJgFD5zDM4iriCCOcQraVZKo8QlkwHPp8pL-CBC1SFXLkhSQJhB8AcItvoXB9SXL-KPC4Jb5vGX6fURpfLq4inlbrG70nHf-1ygTai0VM37t73Hk_QZsXvU4t6p2itmM3lmU4biuS89JdPnwi-Aw
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3JTsMwEB2xSCwHdsSOhbgG2dl9RIWqLKKVaKXeIsdjQwVKKhIO7ddjp2mp4ACXnGxrZM9k5umNnwEuGdMuCooOBq5w_ECamENPO64vPOYi5Tjp8n0KWz3_vh_0a6Bo78IYIwqzUlGR-Daqh6hrhQFmYCSvGMjxIiwH5i9rW7iuG8_fLR1hzW7GnoFEIZ0qCc1PtVlIFnNZaC6dNDehPTOk6iJ5u_os0ys5_qHR-H9Lt2CjrizJ9cQVtmFBZTuw2pg-6LYD63Pag7vQbo3wIzfuQzrKGDFARdrmWx0UyTXpvObF0HIMpGvRtBXhJIOMtN8HL3lmRZDz0s55HmWmhCxUsQe95m230XLq1xUcYSBP6UiBvlZUxSkLYhlFXoRCxj4ilUrHqKXignpmAE91qLlCjHXIA4unqC-p9PZhKcszdQBEcZMAQ66DSEQ-Mh0L7cc0jaQbIfeoOoQzs1FJHR1FUhHfLktmu3QIF9PjSIYTlY3fg47-WuUcVjo3zeTx7unhGNYmND9zWHACS-XHpzo11UOZnlUu8wXvLMCG
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Hydrogen+Peroxide+Oxidation+of+Phosphite+Triesters+in+Oligonucleotide+Syntheses&rft.jtitle=Organic+process+research+%26+development&rft.au=Cvetovich%2C+Raymond+J.&rft.date=2010-01-15&rft.issn=1083-6160&rft.eissn=1520-586X&rft.volume=14&rft.issue=1&rft.spage=295&rft.epage=297&rft_id=info:doi/10.1021%2Fop900044z&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_op900044z
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1083-6160&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1083-6160&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1083-6160&client=summon