A Polar 18 F‐Labeled Amino Acid Derivative for Click Labeling of Biomolecules
This work describes the synthesis and 18 F‐labeling of an amino acid based prosthetic group that is able to participate in copper(I)‐catalyzed cycloadditions. The prosthetic group can be used for 18 F labeling of biomolecules under mild conditions. The synthesis started with L ‐serine methyl ester,...
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| Veröffentlicht in: | European journal of organic chemistry 2014-06, Vol.2014 (17), p.3546-3550 |
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| container_title | European journal of organic chemistry |
| container_volume | 2014 |
| creator | Schieferstein, Hanno Ross, Tobias L. |
| description | This work describes the synthesis and
18
F‐labeling of an amino acid based prosthetic group that is able to participate in copper(I)‐catalyzed cycloadditions. The prosthetic group can be used for
18
F labeling of biomolecules under mild conditions. The synthesis started with
L
‐serine methyl ester, which was derivatized by introducing an alkyne moiety and a leaving group for
18
F labeling. Subsequently,
18
F labeling as well as deprotection conditions were screened, which resulted in an overall radiochemical yield (RCY) of around 28 %. Furthermore, the
18
F‐labeled prosthetic group was treated with an azido cyclic Arg‐Gly‐Asp (cRGD) peptide as a model system in very high RCY of 98 %. |
| doi_str_mv | 10.1002/ejoc.201400071 |
| format | Article |
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18
F‐labeling of an amino acid based prosthetic group that is able to participate in copper(I)‐catalyzed cycloadditions. The prosthetic group can be used for
18
F labeling of biomolecules under mild conditions. The synthesis started with
L
‐serine methyl ester, which was derivatized by introducing an alkyne moiety and a leaving group for
18
F labeling. Subsequently,
18
F labeling as well as deprotection conditions were screened, which resulted in an overall radiochemical yield (RCY) of around 28 %. Furthermore, the
18
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18
F‐labeling of an amino acid based prosthetic group that is able to participate in copper(I)‐catalyzed cycloadditions. The prosthetic group can be used for
18
F labeling of biomolecules under mild conditions. The synthesis started with
L
‐serine methyl ester, which was derivatized by introducing an alkyne moiety and a leaving group for
18
F labeling. Subsequently,
18
F labeling as well as deprotection conditions were screened, which resulted in an overall radiochemical yield (RCY) of around 28 %. Furthermore, the
18
F‐labeled prosthetic group was treated with an azido cyclic Arg‐Gly‐Asp (cRGD) peptide as a model system in very high RCY of 98 %.</description><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNo9kLFOwzAURS0EEqWwMvsHEp7t2I7HEGhBilSGDmxR4jwjl6RGNlRi4xP4Rr6EFhDTvcPRGQ4hlwxyBsCvcBNszoEVAKDZEZkxMCYDZeB4_wtRZMyIx1NyltJmjxil2IysKvoQxi5SVtLF18dn0_U44kCryW8Drawf6A1Gv-te_Q6pC5HWo7fP9Ifz2ycaHL32YQoj2rcR0zk5cd2Y8OJv52S9uF3Xd1mzWt7XVZPZsmAZKiec4rY3qJ0VnGsDUkoQfdFrq0QhB42DtaVAlEqZfhAauYZyUEI6q8Wc5L9aG0NKEV37Ev3UxfeWQXuo0R5qtP81xDfZTlKm</recordid><startdate>201406</startdate><enddate>201406</enddate><creator>Schieferstein, Hanno</creator><creator>Ross, Tobias L.</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201406</creationdate><title>A Polar 18 F‐Labeled Amino Acid Derivative for Click Labeling of Biomolecules</title><author>Schieferstein, Hanno ; Ross, Tobias L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c841-e6f3f62cb9e7fc32279055503b4b7c6345d7edcc83ee5669bd37e2708d635fc73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schieferstein, Hanno</creatorcontrib><creatorcontrib>Ross, Tobias L.</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schieferstein, Hanno</au><au>Ross, Tobias L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Polar 18 F‐Labeled Amino Acid Derivative for Click Labeling of Biomolecules</atitle><jtitle>European journal of organic chemistry</jtitle><date>2014-06</date><risdate>2014</risdate><volume>2014</volume><issue>17</issue><spage>3546</spage><epage>3550</epage><pages>3546-3550</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>This work describes the synthesis and
18
F‐labeling of an amino acid based prosthetic group that is able to participate in copper(I)‐catalyzed cycloadditions. The prosthetic group can be used for
18
F labeling of biomolecules under mild conditions. The synthesis started with
L
‐serine methyl ester, which was derivatized by introducing an alkyne moiety and a leaving group for
18
F labeling. Subsequently,
18
F labeling as well as deprotection conditions were screened, which resulted in an overall radiochemical yield (RCY) of around 28 %. Furthermore, the
18
F‐labeled prosthetic group was treated with an azido cyclic Arg‐Gly‐Asp (cRGD) peptide as a model system in very high RCY of 98 %.</abstract><doi>10.1002/ejoc.201400071</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1434-193X |
| ispartof | European journal of organic chemistry, 2014-06, Vol.2014 (17), p.3546-3550 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_201400071 |
| source | Wiley Online Library Journals Frontfile Complete |
| title | A Polar 18 F‐Labeled Amino Acid Derivative for Click Labeling of Biomolecules |
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