Inquiry Basket
3-(3-Amino-3-carboxypropyl)-1-methylpseudoUridine
The hypermodified residue 1-methyl-3-(3-amino-3-carboxypropyl) pseudoUridine (m1acp3Ψ) was first isolated from the RNA of cells of an established line of cells of Chinese hamster in 1974 and was localized in 18S rRNAs.
* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.
Catalog
BRP-02134
Synonyms
1(2H)-Pyrimidinebutanoic acid, a-amino-3,6-dihydro-3-methyl-2,6-dioxo-5-b-D-ribofuranosyl-; Acpmpsu; 1-Methyl-3-(3-carboxy-3-aminopropyl)-5-(beta-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione; α-Amino-3,6-dihydro-3-methyl-2,6-dioxo-5-β-D-ribofuranosyl-1(2H)-pyrimidinebutanoic acid; 1-Methyl-3-(3-amino-3-carboxypropyl)pseudouridine; 1-Methyl-3-γ-(α-amino-α-carboxypropyl)pseudouridine
CAS
52777-29-4
IUPAC Name
2-amino-4-[5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-methyl-2,6-dioxopyrimidin-1-yl]butanoic acid
Molecular Weight
359.34
Molecular Formula
C14H21N3O8
Canonical SMILES
CN1C=C(C(=O)N(C1=O)CCC(C(=O)O)N)C2C(C(C(O2)CO)O)O
InChI
InChI=1S/C14H21N3O8/c1-16-4-6(11-10(20)9(19)8(5-18)25-11)12(21)17(14(16)24)3-2-7(15)13(22)23/h4,7-11,18-20H,2-3,5,15H2,1H3,(H,22,23)/t7?,8-,9-,10-,11+/m1/s1
InChIKey
CTPQMQZKRWLMRA-LYTXVXJPSA-N
Boiling Point
665.2±65.0 °C at 760 mmHg
Purity
≥99%
Density
1.575±0.06 g/cm3
Appearance
White crystalline powder
Storage
Store at 2-8 °C
Symbol
m1acp3Y
Chemical Structure:
Reference Reading
1. Biosynthesis of a hypermodified nucleotide in Saccharomyces carlsbergensis 17S and HeLa-cell 18S ribosomal ribonucleic acid
R C Brand, J Klootwijk, R J Planta, B E Maden. Biochem J. 1978 Jan 1;169(1):71-7. doi: 10.1042/bj1690071.
The biosynthesis of a hypermodified nucleotide, similar to or identical with 3-(3-amino-3-carboxypropyl)-1-methylpseudouridine monophosphate, present in Saccharomyces carlsbergensis 17S and HeLa-cell 18S rRNA, was investigated with respect to the sequence of reactions required for synthesis and their timing in ribosome maturation. In both yeast and HeLa cells methylation precedes attachment of the 3-amino-3-carboxypropyl group. In yeast the methylated precursor nucleotide was tentatively characterized as 1-methylpseudouridine. This precursor nucleotide was demonstrated in both 37S and most of the cytoplasmic 18S pre-rRNA (rRNA precursor) molecules. The synthesis of the hypermodified nucleotide is completed just before the final cleavage of 18S pre-rRNA to give 17S rRNA, so that the final addition of the 3-amino-3-carboxypropyl group is a cytoplasmic event. Comparable experiments with HeLa cells indicated that formation of 1-methylpseudouridine occurs at the level of 45S RNA and addition of the 3-amino-3-carboxypropyl group occurs in the cytoplasm on newly synthesized 18S RNA.
2. A sequence from Drosophila melanogaster 18S rRNA bearing the conserved hypermodified nucleoside am psi: analysis by reverse transcription and high-performance liquid chromatography
D C Youvan, J E Hearst. Nucleic Acids Res. 1981 Apr 10;9(7):1723-41. doi: 10.1093/nar/9.7.1723.
The naturally occurring modified nucleoside 3-[3-amino-3-carboxypropyl]-1-methylpseudouridine (abbreviated am psi) is found in eukaryotic 18S rRNA. We localized am psi to sequence resolution in D. melanogaster 18S rRNA. This hypermodified base causes an absolute stop in cDNA elongation. The RNA sequence bearing am psi was determined by dideoxy-sequencing with reverse transcriptase. The rDNA coding for this part of the 18S rRNA was sequenced by the Maxam-Gilbert method. Together these two sequencing methods can be used to position the cDNA stop (am psi) in the rRNA sequence. Chemical evidence for the existence of am psi in this RNA sequence was obtained by high-performance liquid chromatography (HPLC) of 18S rRNA nucleosides from radioactive-labeled cells. L-[2-14C] methionine will selectively label am psi in eukaryotic 18S rRNA. Using HPLC, we found a single 14C-labeled nucleotide in digests of 18S rRNA. This nucleotide is in the RNA sequence bearing the cDNA stop since a restriction fragment which hybridizes to this sequence protects the modified base from RNase T1 digestion.
