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Key Documents

M024080

Sigma-Aldrich

ssH-Linker

configured for PerkinElmer, configured for Polygen

Synonym(s):

9,11-Dioxa-2-aza-10-phosphatridecanoic acid, 10-[bis(1-methylethyl)amino]-13-cyano-, 2-[[(4-methoxyphenyl)diphenylmethyl]amino]ethyl este

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About This Item

Empirical Formula (Hill Notation):
C38H53N4O5P
Molecular Weight:
676.83
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.51

type

for DNA synthesis

product line

Proligo Reagents

Assay

≥98% (31P-NMR)
≥98.0% (reversed phase HPLC)

compatibility

configured for PerkinElmer
configured for Polygen

storage temp.

−20°C

SMILES string

COc1ccc(cc1)C(NCCOC(=O)NCCCCCCOP(OCCC#N)N(C(C)C)C(C)C)(c2ccccc2)c3ccccc3

InChI

1S/C38H53N4O5P/c1-31(2)42(32(3)4)48(47-29-16-25-39)46-28-15-7-6-14-26-40-37(43)45-30-27-41-38(33-17-10-8-11-18-33,34-19-12-9-13-20-34)35-21-23-36(44-5)24-22-35/h8-13,17-24,31-32,41H,6-7,14-16,26-30H2,1-5H3,(H,40,43)

InChI key

VTFLXOVDKJUHER-UHFFFAOYSA-N

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General description

ssH-linker comprises an internal carbamate group attached to the MMT-protected amino group via a short spacer. The carbamate moiety facilitates the cleavage of the MMT group under mildly acidic conditions while increasing the stability of the MMT group during the deprotection of the oligonucleotide with ammonia. The carbamate group also enhances the reactivity of the amino group through a neighbor group effect, and thereby accelerates conjugations to amino reactive modifiers and reporters. The MMT-group of ssH-linker serves as an excellent purification handle after the oligonucleotide synthesis in trityl-on mode, similar to the DMT-group of conventional oligonucleotides. The MMT-group is cleaved under very mild conditions in aqueous acetic acid (10% glacial acetic acid in the water, 20 min. room temp.) Alternatively, the MMT-group can be cleaved on the synthesis instrument with an acidic deblock solution to enable on-support labeling protocols.

Legal Information

This product is covered under US Patent Number 7,491,857

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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