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909505

Sigma-Aldrich

C8-Alkyne-dU-CEP

Synonym(s):

5-(Octa-1,7-diynyl)-3′-O-[(2-cyanoethoxy)(diisopropylamino)-phosphono)]-5′-O- (4,4′-dimethoxytrityl)-2′-deoxyuridine, 5-Octadiynyl-dU CEP, C8-Alkyne dU phosphoramidite

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250 MG
$315.00

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250 MG
$315.00

About This Item

Empirical Formula (Hill Notation):
C47H55N4O8P
CAS Number:
938186-76-6
Molecular Weight:
834.94
MDL number:
MFCD10687025
UNSPSC Code:
41116105
NACRES:
NA.22

$315.00

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form

powder

reaction suitability

reaction type: click chemistry

storage temp.

−20°C

SMILES string

P(N(C(C)C)C(C)C)(OC1[C@H](O[C@H](C1)N2C=C(C(=O)NC2=O)C#CCCCCC#C)COC([3H])[2H])OCCC#N

InChI

1S/C27H39N4O6P/c1-7-8-9-10-11-12-14-22-18-30(27(33)29-26(22)32)25-17-23(24(36-25)19-34-6)37-38(35-16-13-15-28)31(20(2)3)21(4)5/h1,18,20-21,23-25H,8-11,13,16-17,19H2,2-6H3,(H,29,32,33)/t23?,24-,25-,38?/m1/s1/i6TD/t6?,23?,24-,25-,38?

InChI key

VMEOYXBOBQPPSL-YSJOBRKDSA-N

Application

This functional phosphoramidite is used to introduce click handles univerally (5′ internal and 3′end) into oligonucleotides under standard conditions for solid phase synthesis. Afterwards the oligonucleotide (RNA, PNA, DNA) can be efficiently conjugated using a copper-catalyzed click reaction to azide-functionalized moieties such as fluorescent dye azides and azido amino acids

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT3730

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Frank Seela et al.
Chemistry & biodiversity, 3(5), 509-514 (2006-12-29)
The synthesis of a series of oligonucleotides containing 5-substituted pyrimidines as well as 7-substituted 7-deazapurines bearing diyne groups with terminal triple bonds is reported. The modified nucleosides were prepared from the corresponding iodo nucleosides and diynes by the Sonogashira cross-coupling
DNA photography: an ultrasensitive DNA-detection method based on photographic techniques.
David M Hammond et al.
Angewandte Chemie (International ed. in English), 46(22), 4184-4187 (2007-04-27)
Dorota I Rozkiewicz et al.
Chembiochem : a European journal of chemical biology, 8(16), 1997-2002 (2007-09-15)
This paper describes a straightforward procedure to immobilize oligonucleotides on glass substrates in well-defined micropatterns by microcontact printing with a dendrimer-modified stamp. The oligonucleotides are efficiently immobilized by "click" chemistry induced by microcontact printing. Acetylene-modified oligonucleotides were treated with an
Johannes Gierlich et al.
Organic letters, 8(17), 3639-3642 (2006-08-11)
[reaction: see text] We report the development of the Cu(I)-catalyzed Huisgen cycloaddition (click) reaction for the multiple postsynthetic labeling of alkyne-modified DNA. A series of alkyne-modified oligodeoxyribonucleotides (ODNs) of increasing alkyne density were prepared, and the click reaction using various

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