Semi-automatic amino acid sequencing and D/L-configuration determination of peptides with detection of liberated N-terminal phenylthiocarbamoylamino acids

Iida, Takayuki; Santa, Tomofumi; Toriba, Akira; Imai, Kazuhiro

doi:10.1039/a806109b

Cited by 9 publications

(6 citation statements)

References 19 publications

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“…We have reported that the use of an aprotic acid, boron trifluoride (BF 3 ), facilitated the cyclization/cleavage reaction and provided higher yields of TZ-amino acids than TFA without racemization of the chiral center of amino acid. 11,[16][17][18] We used TFA since it has usually been used as the cyclization/cleavage reagent and the racemization of TZ-amino acids was not examined in this study. In order to observe the effect of the substituent group on the reaction, the time course of the yield of the TZ-Pro generated from TC-Pro-His-Leu was examined, since the N-terminal Pro-His linkage of a peptide is known to be particularly resistant to cleavage.…”

Section: Cyclization/cleavage Reaction By Tfamentioning

confidence: 99%

Comparison of four fluorescence Edman reagents with benzofurazan structure for the detection of thiazolinone amino acid derivatives

Toriba¹,

Santa²,

Iida³

et al. 1999

Analyst

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Section: Cyclization/cleavage Reaction By Tfamentioning

confidence: 99%

Comparison of four fluorescence Edman reagents with benzofurazan structure for the detection of thiazolinone amino acid derivatives

Toriba¹,

Santa²,

Iida³

et al. 1999

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“…BF 3 etherate (BF 3 ·Et 2 O)-induced Edman degradation in acetonitrile (40 mM BF 3 ·Et 2 O, 5 min) has been reported to reduce proton-catalyzed racemization while completely cleaving PITC-modified N-terminal amino acids. ( 31, 32 ) Moreover, BF 3 methanol complex has been used as a non-depurinating detritylation reagent in DNA synthesis. ( 33 ) Encouraged by these reports, we hypothesized that DNA stability would be enhanced in a cleavage reaction mediated by BF 3 ·Et 2 O in acetonitrile.…”

Section: Resultsmentioning

confidence: 99%

Peptide sequencing via reverse translation of peptides into DNA

Zheng,

Sun,

Eisenstein

et al. 2024

Preprint

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Scalable methods that can accurately sequence peptides at single-amino acid resolution could significantly advance proteomic studies. We present a protein sequencing method based on the “reverse translation” of peptide sequence information into DNA barcodes that document the identity, position, and the originating peptide of each amino acid. We employ a modified Edman degradation process that converts peptides into DNA-barcoded amino acids, which are subsequently detected by proximity extension assay, yielding multi-barcoded DNA outputs that can be PCR amplified and sequenced. Using our method, we sequenced multiple consecutive amino acids within a model peptide. This method also enables the differentiation of single amino acid substitutions, and the identification of post-translational modifications and their positions within multiple peptides simultaneously. With further development, we anticipate that this method will enable highly parallelde novoprotein sequencing with single-molecule sensitivity.

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“…One of the challenges of manual Edman sequencing is the loss of parent peptide, which is caused by incomplete reaction frequently occurred at each cycle. It has been reported that the reaction yield of a gas-phase automated sequencer is extremely high, and a protein containing more than 90 amino acid residues was successfully analyzed by using such a sequencer by Hunkapiller and Hood 50 , 51 . The amino acid sequence and configuration analysis in longer peptides can be completed by the application of a HPLC–MS/CD system coupled to an automated gas-phase peptide sequencer.…”

Section: Resultsmentioning

confidence: 99%

Determination of sequence and absolute configuration of peptide amino acids by HPLC–MS/CD-based detection of liberated N-terminus phenylthiohydantoin amino acids

Hahn

Wang

Choi

et al. 2022

Sci Rep

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We report a method for the simultaneous determination of the sequence and absolute configuration of peptide amino acids using a combination of Edman degradation and HPLC–MS/CD. Phenylthiohydantoin (PTH) derivatives of 20 pairs of standard d- and l-amino acids were synthesized by the Edman reaction. The CD spectra of the derivatives revealed that each pair of the PTH derivatives exhibited the absorption with opposite signs at around 270 nm. These standard PTH derivatives showed well-resolved resolution without interference from byproducts in the ion chromatogram and clear positive/negative CD absorptions when subjected on a reversed phase HPLC–MS system coupled with a CD-2095 HPLC detector. This method was applied for the detection of a synthetic pentapeptide and a natural depsipeptide (halicylindramide C). The sequence and configuration of the pentapeptide and up to eight residues of halicylindramide C were successfully analyzed by this method. The amino acid configuration of the pentapeptide was also determined successfully by subjecting its acid hydrolysates to the Edman reaction followed by HPLC–MS/CD.

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Semi-automatic amino acid sequencing and D/L-configuration determination of peptides with detection of liberated N-terminal phenylthiocarbamoylamino acids

Cited by 9 publications

References 19 publications

Comparison of four fluorescence Edman reagents with benzofurazan structure for the detection of thiazolinone amino acid derivatives

Comparison of four fluorescence Edman reagents with benzofurazan structure for the detection of thiazolinone amino acid derivatives

Peptide sequencing via reverse translation of peptides into DNA

Determination of sequence and absolute configuration of peptide amino acids by HPLC–MS/CD-based detection of liberated N-terminus phenylthiohydantoin amino acids

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