Home Products Modification and Labeling Label Phosphoramidites and Supports GalNAc (N-Acetylgalactosamine) Labeling of Oligonucleotides 5'-GalNAc C3 Phosphoramidite

5'-GalNAc C3 Phosphoramidite - (10-1974)

(4-(Trimethoxytrityloxymethyl)-1-(6-(4-(3,4,6-O-triacetyl-2-acetylamino-2-deoxy-β-D-galactopyranosyl)butanamido)hexanoyl)piperidin-4-yl)methyl-O-[(2-cyanoethyl)-(N,N-diisopropyl)] phosphoramidite

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10-1974

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Product Specifications

Formula:

C₆₂H₈₈N₅O₁₇P

M.W.:

1206.38

F.W.:

609.61

CAS Number:

2437303-51-8

(4-(Trimethoxytrityloxymethyl)-1-(6-(4-(3,4,6-O-triacetyl-2-acetylamino-2-deoxy-β-D-galactopyranosyl)butanamido)hexanoyl)piperidin-4-yl)methyl-O-[(2-cyanoethyl)-(N,N-diisopropyl)] phosphoramidite

Description

A directed approach to the delivery of therapeutic oligonucleotides specifically to the liver has been to target the asialoglycoprotein receptor (ASGPR) using a suitable glycoconjugate. Indeed, ASGPR is the ideal target for delivery of therapeutic oligonucleotides to the liver since it combines tissue specificity, high expression levels and rapid internalization and turnover. The use of oligonucleotide glycoconjugates has led to significant advances in therapeutic delivery as evidenced by the work of Alnylam Pharmaceuticals and Ionis Pharmaceuticals using multivalent N-acetylgalactosamine (GalNAc) oligonucleotide conjugates.

Glen Research is delighted to introduce a GalNAc modification strategy using a monomeric GalNAc support and the equivalent GalNAc phosphoramidite. Our experimental work has shown that these products are fully compatible with regular oligonucleotide synthesis and deprotection. Oligonucleotides containing GalNAc can be deprotected using standard procedures during which the acetyl protecting groups on the GalNAc group are removed. We have demonstrated that 5’-GalNAc C3 phosphoramidite can be used to prepare oligonucleotides with multiple consecutive GalNAc additions at the 5’ terminus.

Glen Research offers these GalNAc C3 products under an agreement with AM Chemicals LLC.

Details

Usage

Coupling: 12 minute coupling time is recommended.
Deprotection: As required by nucleobases. Compatible with 30% ammonium hydroxide for 2 hours at 65°C, 17 hours at room temperature, AMA (ammonium hydroxide/40% methylamine 1:1) for 10 minutes at 65 °C and UltraMild deprotection conditions. Note extended deprotection in ammonium hydroxide (17 hours at 55 °C) will lead to some degradation.

Specifications
Diluent	Anhydrous Acetonitrile
Recommended Storage	Refrigerated storage, maximum of 2-8°C, dry
Stability In Solution	1-2 Days

Dilution/Coupling Data

The table below show pack size data and, for solutions, dilution and approximate coupling based on normal priming procedures.

ABI 392/394

Catalog #	Pack Size	Grams/Pack	0.1M Dil. (mL)	Approximate Number of Additions
				LV40	LV200	40nm	0.2μm	1μm	10μm
10-1974-02	0.25 g	.25grams	2.07	55.67	33.4	20.88	15.18	11.13	2.78
10-1974-90	100 µmol	.121grams	1	20	12	7.5	5.45	4	1
10-1974-95	50 µmol	.06grams	0.5	3.33	2	1.25	0.91	0.67	0.17

Expedite

Catalog #	Pack Size	Grams/Pack	Dilution (mL)	Approximate Number of Additions
				Molarity	50nm	0.2μm	1μm	15μm
10-1974-02	0.25 g	.25grams	3.09	0.07	55.4	34.63	25.18	3.46
10-1974-90	100 µmol	.121grams	1.5	0.07	23.6	14.75	10.73	1.48
10-1974-95	50 µmol	.06grams	0.75	0.07	8.6	5.38	3.91	0.54