Abstract
The elaboration of misacylated transfer RNAs by T4 RNA ligase-mediated condensation of an aminoacylated pdCpA derivative and a tRNA (transcript) missing the two 3′-terminal nucleotides requires that the aminoacyl moiety of the dinucleotide be stabilized during the ligation reaction. This can be done conveniently by the use of a simple 4-pentenoyl group attached to N α of the amino acid. The pentenoyl amide can be deblocked readily with aqueous iodine, presumably via an iodolactone intermediate. This protecting group can be used in conjunction with side chain protecting group for amino acids having side chain functionality, thus permitting the elaboration of proteins bearing side chain protecting groups that can be removed in a subsequent step (e.g., caged proteins). In addition, an aminated analogue of the pentenoyl protecting group, the unnatural amino acid allylglycine, can be employed as part of the peptide backbone to afford a protein cleavable by iodine.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 245-251 |
| Number of pages | 7 |
| Journal | Methods |
| Volume | 36 |
| Issue number | 3 |
| DOIs | |
| State | Published - Jul 2005 |
| Externally published | Yes |
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Keywords
- Amino acid protecting group
- Cleavable proteins
- Misacylated transfer RNAs
- Protein synthesis
ASJC Scopus subject areas
- Molecular Biology
Cite this
The N-pentenoyl protecting group for aminoacyl-tRNAs. / Lodder, Michiel; Wang, Bixun; Hecht, Sidney.
In: Methods, Vol. 36, No. 3, 07.2005, p. 245-251.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The N-pentenoyl protecting group for aminoacyl-tRNAs
AU - Lodder, Michiel
AU - Wang, Bixun
AU - Hecht, Sidney
PY - 2005/7
Y1 - 2005/7
N2 - The elaboration of misacylated transfer RNAs by T4 RNA ligase-mediated condensation of an aminoacylated pdCpA derivative and a tRNA (transcript) missing the two 3′-terminal nucleotides requires that the aminoacyl moiety of the dinucleotide be stabilized during the ligation reaction. This can be done conveniently by the use of a simple 4-pentenoyl group attached to N α of the amino acid. The pentenoyl amide can be deblocked readily with aqueous iodine, presumably via an iodolactone intermediate. This protecting group can be used in conjunction with side chain protecting group for amino acids having side chain functionality, thus permitting the elaboration of proteins bearing side chain protecting groups that can be removed in a subsequent step (e.g., caged proteins). In addition, an aminated analogue of the pentenoyl protecting group, the unnatural amino acid allylglycine, can be employed as part of the peptide backbone to afford a protein cleavable by iodine.
AB - The elaboration of misacylated transfer RNAs by T4 RNA ligase-mediated condensation of an aminoacylated pdCpA derivative and a tRNA (transcript) missing the two 3′-terminal nucleotides requires that the aminoacyl moiety of the dinucleotide be stabilized during the ligation reaction. This can be done conveniently by the use of a simple 4-pentenoyl group attached to N α of the amino acid. The pentenoyl amide can be deblocked readily with aqueous iodine, presumably via an iodolactone intermediate. This protecting group can be used in conjunction with side chain protecting group for amino acids having side chain functionality, thus permitting the elaboration of proteins bearing side chain protecting groups that can be removed in a subsequent step (e.g., caged proteins). In addition, an aminated analogue of the pentenoyl protecting group, the unnatural amino acid allylglycine, can be employed as part of the peptide backbone to afford a protein cleavable by iodine.
KW - Amino acid protecting group
KW - Cleavable proteins
KW - Misacylated transfer RNAs
KW - Protein synthesis
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U2 - 10.1016/j.ymeth.2005.04.002
DO - 10.1016/j.ymeth.2005.04.002
M3 - Article
VL - 36
SP - 245
EP - 251
JO - Methods
JF - Methods
SN - 1046-2023
IS - 3
ER -