1956
DOI: 10.1021/ja01588a027
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N-Tritylamino Acids and Peptides. A New Method of Peptide Synthesis1

Abstract: A method of peptide synthesis is described in which the trityl group is used to protect the amino group of amino acids and peptides. These trityl derivatives are coupled with other amino acids by the usual methods. The trityl group is removed under mild conditions, e.g., by acetic acid, by one equivalent of hydrochloric acid or by catalytic hydrogenation.

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Cited by 157 publications
(58 citation statements)
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“…Further experiments were directed towards on-resin oxidative deblocking of tBu protection using Tl(tfa) 3 . 20 The fully protected Boc-DPhe 1 -Ncy(tBu) 2 -Phe 3 -DTrp(Boc) 4 -Lys(Boc) 5 -Thr(tBu) 6 -Ncy(tBu) 7 -Thr (tBu) 8 All of the crude peptides (7-9) were purified 21 by RP-HPLC in at least two different solvent systems (TEAP pH 2.25 and 0.1% TFA on C 18 silica). The analytical techniques used for the characterization of the analogs in Table 1 octreotide-amide synthesized in parallel using resolved Boc-Ncy(Mob)-OH 1 and Bocstrategy.…”
Section: Nih Public Accessmentioning
confidence: 99%
“…Further experiments were directed towards on-resin oxidative deblocking of tBu protection using Tl(tfa) 3 . 20 The fully protected Boc-DPhe 1 -Ncy(tBu) 2 -Phe 3 -DTrp(Boc) 4 -Lys(Boc) 5 -Thr(tBu) 6 -Ncy(tBu) 7 -Thr (tBu) 8 All of the crude peptides (7-9) were purified 21 by RP-HPLC in at least two different solvent systems (TEAP pH 2.25 and 0.1% TFA on C 18 silica). The analytical techniques used for the characterization of the analogs in Table 1 octreotide-amide synthesized in parallel using resolved Boc-Ncy(Mob)-OH 1 and Bocstrategy.…”
Section: Nih Public Accessmentioning
confidence: 99%
“…The method used was a modified version of the method described by Zervas and Theodoropoulos (40). To a stirred solution of ethyl 8-aminooctanoate (190.9 mg, 1.02 mmol) dissolved in 5 mL of chloroform were added triethylamine (103.7 mg, 1.02 mmol) and trityl chloride (1.05 equiv.).…”
Section: N-trityl Erhyl 8-arninoocranoarementioning
confidence: 99%
“…It was therefore decided to attach N-tritylamino acids to the side chain amino group of the nucleotide ( Figure 5). In previous work in our laboratory, [19,20] N-trityl derivatives of different substituted phenylalanines, glycine and histidine were prepared by the method of Zervas and Theodoropoulos [21] and attached to puromycin amino nucleoside (PANS) for studies on protein synthesis. Couplings of N-trityl amino acids to PANS were facilitated by NHS activation of carboxyl groups.…”
Section: Resultsmentioning
confidence: 99%
“…N-Tritylglycine (9) and the N-trityl derivatives of o-(10), m-(11) and p-(12) fluorophenylalanine were prepared by Nel and Ariatti [19] using the method of Zervas and Theodoropoulos. [21] The N-hydroxysuccinimide derivative of N-trityl-m-fluorophenylalanine (6) was prepared from 11 by the procedure of Nel and Ariatti. [19] Assay for RNA-Dependent DNA Polymerase Activity of M-MuLV Reverse Transcriptase The nucleotide-palmitate compound (2, Figure 1) was also solubilized in an aqueous solution as follows: An EtOH solution of nucleotide-palmitate (400 µg/40 µl) was taken to dryness and the residue suspended in 500 µl H 2 O.…”
Section: Methodsmentioning
confidence: 99%