Quantitation of Cysteine Residues Alkylated with 3-Bromopropylamine by Amino Acid Analysis
A new versatile reagent, 3-bromopropylamine, for the quantitative analysis of cysteine residues in proteins and peptides is reported. When added to amino acid standards, the 3-bromopropylamine derivative of cysteine, S-3-aminopropylcysteine, elutes in a unique position on four different amino acid a...
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| Veröffentlicht in: | Analytical biochemistry 1994-01, Vol.216 (1), p.61-66 |
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| container_title | Analytical biochemistry |
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| creator | Hale, J.E. Beidler, D.E. Jue, R.A. |
| description | A new versatile reagent, 3-bromopropylamine, for the quantitative analysis of cysteine residues in proteins and peptides is reported. When added to amino acid standards, the 3-bromopropylamine derivative of cysteine, S-3-aminopropylcysteine, elutes in a unique position on four different amino acid analysis systems without modification to their standard gradients. Optimized conditions for the complete alkylation of cysteines in proteins with 3-bromopropylamine are described. The S-3-aminopropylcysteine is stable to standard acid hydrolysis conditions used for amino acid analysis. Cysteine values are within 10% of the predicted value in the amino acid analysis of acid hydrolysates of known proteins based on quantitation with S-3-aminopropylcysteine. No evidence of alkylation of other amino acids by 3-bromopropylamine is apparent from the amino acid analysis of proteins alkylated under the optimal conditions. These results expand the application of 3-bromopropylamine to include quantitation of cysteine by amino acid analysis as well as the previously reported identification of cysteines by protein sequencing. |
| doi_str_mv | 10.1006/abio.1994.1008 |
| format | Article |
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When added to amino acid standards, the 3-bromopropylamine derivative of cysteine, S-3-aminopropylcysteine, elutes in a unique position on four different amino acid analysis systems without modification to their standard gradients. Optimized conditions for the complete alkylation of cysteines in proteins with 3-bromopropylamine are described. The S-3-aminopropylcysteine is stable to standard acid hydrolysis conditions used for amino acid analysis. Cysteine values are within 10% of the predicted value in the amino acid analysis of acid hydrolysates of known proteins based on quantitation with S-3-aminopropylcysteine. No evidence of alkylation of other amino acids by 3-bromopropylamine is apparent from the amino acid analysis of proteins alkylated under the optimal conditions. These results expand the application of 3-bromopropylamine to include quantitation of cysteine by amino acid analysis as well as the previously reported identification of cysteines by protein sequencing.</description><identifier>ISSN: 0003-2697</identifier><identifier>EISSN: 1096-0309</identifier><identifier>DOI: 10.1006/abio.1994.1008</identifier><identifier>PMID: 8135367</identifier><identifier>CODEN: ANBCA2</identifier><language>eng</language><publisher>San Diego, CA: Elsevier Inc</publisher><subject>Alkylation ; Amino Acids - analysis ; Analytical, structural and metabolic biochemistry ; Biological and medical sciences ; Cysteine - analysis ; Fundamental and applied biological sciences. Psychology ; General aspects, investigation methods ; Propylamines ; Proteins</subject><ispartof>Analytical biochemistry, 1994-01, Vol.216 (1), p.61-66</ispartof><rights>1994 Academic Press</rights><rights>1994 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-137523f9979420c0a0e0c4657989640309f38ca70a14f7c160a4778b480f73023</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1006/abio.1994.1008$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,4022,27922,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3902489$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8135367$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hale, J.E.</creatorcontrib><creatorcontrib>Beidler, D.E.</creatorcontrib><creatorcontrib>Jue, R.A.</creatorcontrib><title>Quantitation of Cysteine Residues Alkylated with 3-Bromopropylamine by Amino Acid Analysis</title><title>Analytical biochemistry</title><addtitle>Anal Biochem</addtitle><description>A new versatile reagent, 3-bromopropylamine, for the quantitative analysis of cysteine residues in proteins and peptides is reported. When added to amino acid standards, the 3-bromopropylamine derivative of cysteine, S-3-aminopropylcysteine, elutes in a unique position on four different amino acid analysis systems without modification to their standard gradients. Optimized conditions for the complete alkylation of cysteines in proteins with 3-bromopropylamine are described. The S-3-aminopropylcysteine is stable to standard acid hydrolysis conditions used for amino acid analysis. Cysteine values are within 10% of the predicted value in the amino acid analysis of acid hydrolysates of known proteins based on quantitation with S-3-aminopropylcysteine. No evidence of alkylation of other amino acids by 3-bromopropylamine is apparent from the amino acid analysis of proteins alkylated under the optimal conditions. These results expand the application of 3-bromopropylamine to include quantitation of cysteine by amino acid analysis as well as the previously reported identification of cysteines by protein sequencing.</description><subject>Alkylation</subject><subject>Amino Acids - analysis</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Biological and medical sciences</subject><subject>Cysteine - analysis</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects, investigation methods</subject><subject>Propylamines</subject><subject>Proteins</subject><issn>0003-2697</issn><issn>1096-0309</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1994</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kM1r3DAQxUVpSDZpr70FdCi9eTOyZH0c3aX5gEBIaC-9CK0sUyW2tZW0Kf7vK7NLbjmNZuY3j6eH0BcCawLAr8zWhzVRii2t_IBWBBSvgIL6iFYAQKuaK3GGzlN6BiCENfwUnUpCG8rFCv1-3Jsp-2yyDxMOPd7MKTs_Ofzkku_2LuF2eJkHk12H__n8B9Pqewxj2MWwK-NxQbczbssj4Nb6DreTGebk0yd00pshuc_HeoF-Xf_4ubmt7h9u7jbtfWUpl7kiVDQ17ZUSitVgwYADy3gjlFScLR_pqbRGgCGsF5ZwMEwIuWUSekGhphfo20G3WPpbDGc9-mTdMJjJhX3SoqhAI1kB1wfQxpBSdL3eRT-aOGsCeglTL2HqJcylleXg8qi8346ue8OP6ZX91-PeJGuGPprJ-vSGUQU1k6pg8oC5ksKrd1En691kXeejs1l3wb_n4D_Zx45i</recordid><startdate>199401</startdate><enddate>199401</enddate><creator>Hale, J.E.</creator><creator>Beidler, D.E.</creator><creator>Jue, R.A.</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>199401</creationdate><title>Quantitation of Cysteine Residues Alkylated with 3-Bromopropylamine by Amino Acid Analysis</title><author>Hale, J.E. ; Beidler, D.E. ; Jue, R.A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-137523f9979420c0a0e0c4657989640309f38ca70a14f7c160a4778b480f73023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><topic>Alkylation</topic><topic>Amino Acids - analysis</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Biological and medical sciences</topic><topic>Cysteine - analysis</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects, investigation methods</topic><topic>Propylamines</topic><topic>Proteins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hale, J.E.</creatorcontrib><creatorcontrib>Beidler, D.E.</creatorcontrib><creatorcontrib>Jue, R.A.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Analytical biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hale, J.E.</au><au>Beidler, D.E.</au><au>Jue, R.A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Quantitation of Cysteine Residues Alkylated with 3-Bromopropylamine by Amino Acid Analysis</atitle><jtitle>Analytical biochemistry</jtitle><addtitle>Anal Biochem</addtitle><date>1994-01</date><risdate>1994</risdate><volume>216</volume><issue>1</issue><spage>61</spage><epage>66</epage><pages>61-66</pages><issn>0003-2697</issn><eissn>1096-0309</eissn><coden>ANBCA2</coden><abstract>A new versatile reagent, 3-bromopropylamine, for the quantitative analysis of cysteine residues in proteins and peptides is reported. When added to amino acid standards, the 3-bromopropylamine derivative of cysteine, S-3-aminopropylcysteine, elutes in a unique position on four different amino acid analysis systems without modification to their standard gradients. Optimized conditions for the complete alkylation of cysteines in proteins with 3-bromopropylamine are described. The S-3-aminopropylcysteine is stable to standard acid hydrolysis conditions used for amino acid analysis. Cysteine values are within 10% of the predicted value in the amino acid analysis of acid hydrolysates of known proteins based on quantitation with S-3-aminopropylcysteine. No evidence of alkylation of other amino acids by 3-bromopropylamine is apparent from the amino acid analysis of proteins alkylated under the optimal conditions. These results expand the application of 3-bromopropylamine to include quantitation of cysteine by amino acid analysis as well as the previously reported identification of cysteines by protein sequencing.</abstract><cop>San Diego, CA</cop><pub>Elsevier Inc</pub><pmid>8135367</pmid><doi>10.1006/abio.1994.1008</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0003-2697 |
| ispartof | Analytical biochemistry, 1994-01, Vol.216 (1), p.61-66 |
| issn | 0003-2697 1096-0309 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_76400584 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Alkylation Amino Acids - analysis Analytical, structural and metabolic biochemistry Biological and medical sciences Cysteine - analysis Fundamental and applied biological sciences. Psychology General aspects, investigation methods Propylamines Proteins |
| title | Quantitation of Cysteine Residues Alkylated with 3-Bromopropylamine by Amino Acid Analysis |
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