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A novel method for the amino acid sequence/configuration determination of peptides containing D/L-amino acids utilizing a fluorogenic Edman reagent, 7-N,N-dimethylaminosulphonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate (DBD-NCS).
Biomed Chromatogr. 1995 May-Jun; 9(3):152-4.BC

Abstract

A novel method for the amino acid sequence and configuration determination of peptides containing D- or L-amino acids is presented. An enkephalin analogue, [D-Ala2, D-Leu5]enkephalin (Tyr-Ala-Gly-Phe-Leu) was derivatized with a fluorogenic Edman reagent, 7-N,N-dimethylaminosulphonyl-4-(2,1,3-benzoxadiazolyl) isothiocyanate (DBD-NCS), cleaved and cyclized with trifluoroacetic acid at 50 degrees C for 1 min and the resultant thiazolinone derivative (DBD-thiazolinyl-L-Tyr) was separated from the racemized DBD-thiazolinyl-D-Tyr (about 20% as compared to the L-isomer) on a phenylcarbamylated cyclodextrin column: The separation factor (alpha) for D- and L-isomers was 1.09. The column eluate was monitored fluorometrically at 524 nm with excitation at 387 nm. The detection limit was about pmol range. The same treatment adopted for the residual peptide, Ala-Gly-Phe-Leu, gave DBD-thiazolinyl-D-Ala (alpha = 1.09 for D,L-Phe) with the lesser amount of L-analogue (about 20%). In the same manner, Gly and L-Phe (alpha = 1.09) were detected. The method might be useful for the study of aging of proteins such as eye lens and amyloid proteins derived from Alzheimer's disease.

Authors+Show Affiliations

Imai K
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
Matsunaga H
No affiliation info available
Fukushima T
No affiliation info available
Santa T
No affiliation info available
Homma H
No affiliation info available
Nakashima K
No affiliation info available
Akiyama S
No affiliation info available

MeSH

Amino Acid SequenceAmino AcidsChromatography, High Pressure LiquidFluorescent DyesIsothiocyanatesMolecular Sequence DataOxadiazolesPeptidesSequence AnalysisSpectrometry, Fluorescence

Pub Type(s)

Journal Article

Language

eng

PubMed ID

7655305

Citation

Imai, K, et al. "A Novel Method for the Amino Acid Sequence/configuration Determination of Peptides Containing D/L-amino Acids Utilizing a Fluorogenic Edman Reagent, 7-N,N-dimethylaminosulphonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate (DBD-NCS)." Biomedical Chromatography : BMC, vol. 9, no. 3, 1995, pp. 152-4.
Imai K, Matsunaga H, Fukushima T, et al. A novel method for the amino acid sequence/configuration determination of peptides containing D/L-amino acids utilizing a fluorogenic Edman reagent, 7-N,N-dimethylaminosulphonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate (DBD-NCS). Biomed Chromatogr. 1995;9(3):152-4.
Imai, K., Matsunaga, H., Fukushima, T., Santa, T., Homma, H., Nakashima, K., & Akiyama, S. (1995). A novel method for the amino acid sequence/configuration determination of peptides containing D/L-amino acids utilizing a fluorogenic Edman reagent, 7-N,N-dimethylaminosulphonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate (DBD-NCS). Biomedical Chromatography : BMC, 9(3), 152-4.
Imai K, et al. A Novel Method for the Amino Acid Sequence/configuration Determination of Peptides Containing D/L-amino Acids Utilizing a Fluorogenic Edman Reagent, 7-N,N-dimethylaminosulphonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate (DBD-NCS). Biomed Chromatogr. 1995 May-Jun;9(3):152-4. PubMed PMID: 7655305.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A novel method for the amino acid sequence/configuration determination of peptides containing D/L-amino acids utilizing a fluorogenic Edman reagent, 7-N,N-dimethylaminosulphonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate (DBD-NCS). AU - Imai,K, AU - Matsunaga,H, AU - Fukushima,T, AU - Santa,T, AU - Homma,H, AU - Nakashima,K, AU - Akiyama,S, PY - 1995/5/1/pubmed PY - 1995/5/1/medline PY - 1995/5/1/entrez SP - 152 EP - 4 JF - Biomedical chromatography : BMC JO - Biomed Chromatogr VL - 9 IS - 3 N2 - A novel method for the amino acid sequence and configuration determination of peptides containing D- or L-amino acids is presented. An enkephalin analogue, [D-Ala2, D-Leu5]enkephalin (Tyr-Ala-Gly-Phe-Leu) was derivatized with a fluorogenic Edman reagent, 7-N,N-dimethylaminosulphonyl-4-(2,1,3-benzoxadiazolyl) isothiocyanate (DBD-NCS), cleaved and cyclized with trifluoroacetic acid at 50 degrees C for 1 min and the resultant thiazolinone derivative (DBD-thiazolinyl-L-Tyr) was separated from the racemized DBD-thiazolinyl-D-Tyr (about 20% as compared to the L-isomer) on a phenylcarbamylated cyclodextrin column: The separation factor (alpha) for D- and L-isomers was 1.09. The column eluate was monitored fluorometrically at 524 nm with excitation at 387 nm. The detection limit was about pmol range. The same treatment adopted for the residual peptide, Ala-Gly-Phe-Leu, gave DBD-thiazolinyl-D-Ala (alpha = 1.09 for D,L-Phe) with the lesser amount of L-analogue (about 20%). In the same manner, Gly and L-Phe (alpha = 1.09) were detected. The method might be useful for the study of aging of proteins such as eye lens and amyloid proteins derived from Alzheimer's disease. SN - 0269-3879 UR - https://www.unboundmedicine.com/medline/citation/7655305/A_novel_method_for_the_amino_acid_sequence/configuration_determination_of_peptides_containing_D/L_amino_acids_utilizing_a_fluorogenic_Edman_reagent_7_NN_dimethylaminosulphonyl_4__213_benzoxadiazolyl_isothiocyanate__DBD_NCS__ L2 - https://doi.org/10.1002/bmc.1130090309 DB - PRIME DP - Unbound Medicine ER -

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