<a href="https://www.the-hive.ws/forum/showflat.pl?Number=476288&page=48&view=&sort=5&Search=&vc=&new=&start=0&xrated=y&&URLForums=" title="Click here to show this downrated post">phenylalanine as a precursor - a different angle</a> (Rated as: UTFSE!) </td> <td class="text_bg" align="right" valign="top"> </td> <td> </td> </tr> <tr class="text_bg"> <td align="left" valign="bottom"><img src="../forum/images/left_bottom.gif" border="0" height="12" width="9"></td> <td valign="middle" align="center" colspan="7"> </td> <td align="right" valign="bottom"><img src="../forum/images/right_bottom.gif" border="0" height="12" width="9"></td> </tr> <tr class="page_bg"> <td colspan="9"> </td> </tr> <td align="left" valign="top" class="text_bg"> <img src="../forum/images/left_top.gif" border="0" height="12" width="9"></td> <td colspan="7"><a name="Post476686"></a></a> </td> <td align="right" valign="top"><img src="../forum/images/right_top.gif" border="0" height="12" width="9"></td> </tr> <tr class="text_bg"> <td rowspan="2"> </td> <td rowspan="2"> </td> <td valign="top" align="center" rowspan="2"> elfspice (Stranger) 12-13-03 18:22 No 476686 </td> <td rowspan="2"> </td> <td rowspan="2" width="1" class="vert_ruler"> <img src="../forum/images/hr.gif" border="0" width="1" height="1"> </td> <td rowspan="2"> </td> <td class="text_bg" align="left" valign="top"> um i guess that idea has already been written... </td> <td class="text_bg" align="right" valign="top"> </td> <td> </td> </tr> <tr class="text_bg"> <td colspan="2" valign="top" align="left"> um i guess that idea has already been written up somewhere then... i thought i was just tying a bunch of things together </td> <td> </td> </tr> <tr class="text_bg"> <td align="left" valign="bottom"><img src="../forum/images/left_bottom.gif" border="0" height="12" width="9"></td> <td valign="middle" align="center" colspan="7"> </td> <td align="right" valign="bottom"><img src="../forum/images/right_bottom.gif" border="0" height="12" width="9"></td> </tr> <tr class="page_bg"> <td colspan="9"> </td> </tr> <td align="left" valign="top" class="text_bg"> <img src="../forum/images/left_top.gif" border="0" height="12" width="9"></td> <td colspan="7"><a name="Post478972"></a></a> </td> <td align="right" valign="top"><img src="../forum/images/right_top.gif" border="0" height="12" width="9"></td> </tr> <tr class="text_bg"> <td rowspan="2"> </td> <td rowspan="2"> </td> <td valign="top" align="center" rowspan="2"> zwackelmann (Stranger) 12-25-03 05:17 No 478972 </td> <td rowspan="2"> </td> <td rowspan="2" width="1" class="vert_ruler"> <img src="../forum/images/hr.gif" border="0" width="1" height="1"> </td> <td rowspan="2"> </td> <td class="text_bg" align="left" valign="top"> amino acids as precursors </td> <td class="text_bg" align="right" valign="top"> </td> <td> </td> </tr> <tr class="text_bg"> <td colspan="2" valign="top" align="left"> I don´t think the proposed degradation to an aldehyde followed by imine and Grignard is the way of choice to do it. Otherwise this would have become more popular by now. Aromatic acetaldehydes are rather sensitive and tend to give messy mixtures... But! Has any bee experience with esterification of amino acids? Once I had to esterify l-prolin, tried to do so with some alcohol and lots of p-toluenesulfonic acid. The product, an oil (as freebase), seemed o.k. and we thought we had it, apart from the fact that it wouldn´t react at all the way we intended it to do and then we decided it was probably something else. The reason why I go at length into this question is of course that it would be too nice to prepare the esters of phenylalanine and tryptophane and to remove the OH group reductively to yield the corresponding aminoalkyl sidechain. There is a really wonderful way to reduce esters to the corresponding alcohols by treatment with NaBH4/anhydrous LiCl in THF. Yields about 100%! In case THF is difficult to get even Isopropanol works but part of the NaBH4 gets lost due to side-reaction and the reduction is not so complete. Now what could be done with the resulting amino alcohol? Is there a simple way to reduce the CH2OH group to the CH3? Something like protecting the NH2 and esterifying the OH group with p-toluenesulfonic acid chloride, which upon reduction with LiALH4 should leave a methyl group. What would happen if the unprotected NH2 was reacted to the sulfonamide and this was subjected to the LiAlH4 reduction? Will a hydrolyzable N-S-bond be the consequence? Or if the amino alcohol was treated with SO2Cl2? Will it form a cyclic product which upon reduction gives the aminoalkyl-chain? Any bee with information on this? </td> <td> </td> </tr> <tr class="text_bg"> <td align="left" valign="bottom"><img src="../forum/images/left_bottom.gif" border="0" height="12" width="9"></td> <td valign="middle" align="center" colspan="7"> </td> <td align="right" valign="bottom"><img src="../forum/images/right_bottom.gif" border="0" height="12" width="9"></td> </tr> <tr class="page_bg"> <td colspan="9"> </td> </tr> <td align="left" valign="top" class="text_bg"> <img src="../forum/images/left_top.gif" border="0" height="12" width="9"></td> <td colspan="7"><a name="Post479094"></a><a name="last"></a></a> </td> <td align="right" valign="top"><img src="../forum/images/right_top.gif" border="0" height="12" width="9"></td> </tr> <tr class="text_bg"> <td rowspan="2"> </td> <td rowspan="2"> </td> <td valign="top" align="center" rowspan="2"> biotechdude (Hive Bee) 12-26-03 00:35 No 479094 </td> <td rowspan="2"> </td> <td rowspan="2" width="1" class="vert_ruler"> <img src="../forum/images/hr.gif" border="0" width="1" height="1"> </td> <td rowspan="2"> </td> <td class="text_bg" align="left" valign="top"> Phe - Does work; but dont know how </td> <td class="text_bg" align="right" valign="top"> </td> <td> </td> </tr> <tr class="text_bg"> <td colspan="2" valign="top" align="left"> Swix has heard of big-bees who use phenylalanine as their major precurser. They keep their methods secret..(doh!) This doesn't directly help, but gives hope that there is a light at the end of a certain tunnel. Swix wants to go down the AA tunnel soon but has no idea how. Perhaps other AA's contain the right side chains? What are the chains wanted/needed? Swix knows AA's well so me bee able to help... <hr>No Fucking Idea </td> <td> </td> </tr> <tr class="text_bg"> <td align="left" valign="bottom"><img src="../forum/images/left_bottom.gif" border="0" height="12" width="9"></td> <td valign="middle" align="center" colspan="7"> </td> <td align="right" valign="bottom"><img src="../forum/images/right_bottom.gif" border="0" height="12" width="9"></td> </tr> <tr class="page_bg"> <td colspan="9"> </td> </tr> </body> </html>

phenylalanine as a precursor - a different angle , Hive Stimulants


		elfspice 12-11-03 18:50				<a href="https://www.the-hive.ws/forum/showflat.pl?Number=476288&page=48&view=&sort=5&Search=&vc=&new=&start=0&xrated=y&&URLForums=" title="Click here to show this downrated post">phenylalanine as a precursor - a different angle</a> <br> <i title="This post has been downrated by the moderators">(Rated as: UTFSE!)</i> </td> <td class="text_bg" align="right" valign="top"> </td> <td> </td> </tr> <tr class="text_bg"> <td align="left" valign="bottom"><img src="../forum/images/left_bottom.gif" border="0" height="12" width="9"></td> <td valign="middle" align="center" colspan="7"> </td> <td align="right" valign="bottom"><img src="../forum/images/right_bottom.gif" border="0" height="12" width="9"></td> </tr> <tr class="page_bg"> <td colspan="9"> </td> </tr> <td align="left" valign="top" class="text_bg"> <img src="../forum/images/left_top.gif" border="0" height="12" width="9"></td> <td colspan="7"><a name="Post476686"></a></a> </td> <td align="right" valign="top"><img src="../forum/images/right_top.gif" border="0" height="12" width="9"></td> </tr> <tr class="text_bg"> <td rowspan="2"> </td> <td rowspan="2"> </td> <td valign="top" align="center" rowspan="2"> elfspice<br> <i>(<span title="The user's title at the time of posting">Stranger</span>)</i><br> <span title="Posting date">12-13-03 18:22</span><br> <span title="Link to this post by using the markup [476686]">No 476686</span><br> </td> <td rowspan="2"> </td> <td rowspan="2" width="1" class="vert_ruler"> <img src="../forum/images/hr.gif" border="0" width="1" height="1"> </td> <td rowspan="2"> </td> <td class="text_bg" align="left" valign="top"> <b title="The subject of this post">um i guess that idea has already been written...</b> </td> <td class="text_bg" align="right" valign="top"> </td> <td> </td> </tr> <tr class="text_bg"> <td colspan="2" valign="top" align="left"> <br> um i guess that idea has already been written up somewhere then... i thought i was just tying a bunch of things together </td> <td> </td> </tr> <tr class="text_bg"> <td align="left" valign="bottom"><img src="../forum/images/left_bottom.gif" border="0" height="12" width="9"></td> <td valign="middle" align="center" colspan="7"> </td> <td align="right" valign="bottom"><img src="../forum/images/right_bottom.gif" border="0" height="12" width="9"></td> </tr> <tr class="page_bg"> <td colspan="9"> </td> </tr> <td align="left" valign="top" class="text_bg"> <img src="../forum/images/left_top.gif" border="0" height="12" width="9"></td> <td colspan="7"><a name="Post478972"></a></a> </td> <td align="right" valign="top"><img src="../forum/images/right_top.gif" border="0" height="12" width="9"></td> </tr> <tr class="text_bg"> <td rowspan="2"> </td> <td rowspan="2"> </td> <td valign="top" align="center" rowspan="2"> zwackelmann<br> <i>(<span title="The user's title at the time of posting">Stranger</span>)</i><br> <span title="Posting date">12-25-03 05:17</span><br> <span title="Link to this post by using the markup [478972]">No 478972</span><br> </td> <td rowspan="2"> </td> <td rowspan="2" width="1" class="vert_ruler"> <img src="../forum/images/hr.gif" border="0" width="1" height="1"> </td> <td rowspan="2"> </td> <td class="text_bg" align="left" valign="top"> <b title="The subject of this post">amino acids as precursors</b> </td> <td class="text_bg" align="right" valign="top"> </td> <td> </td> </tr> <tr class="text_bg"> <td colspan="2" valign="top" align="left"> <br> I don´t think the proposed degradation to an aldehyde followed by imine and Grignard is the way of choice to do it. Otherwise this would have become more popular by now.<br>Aromatic acetaldehydes are rather sensitive and tend to give messy mixtures...<br>But! Has any bee experience with esterification of amino acids?<br>Once I had to esterify l-prolin, tried to do so with some alcohol and lots of p-toluenesulfonic acid. The product, an oil (as freebase), seemed o.k. and we thought we had it, apart from the fact that it wouldn´t react at all the way we intended it to do and then we decided it was probably something else.<br>The reason why I go at length into this question is of course that it would be too nice to prepare the esters of phenylalanine and tryptophane and to remove the OH group reductively to yield the corresponding aminoalkyl sidechain.<br>There is a really wonderful way to reduce esters to the corresponding alcohols by treatment with NaBH4/anhydrous LiCl in THF. Yields about 100%! In case THF is difficult to get even Isopropanol works but part of the NaBH4 gets lost due to side-reaction and the reduction is not so complete.<br>Now what could be done with the resulting amino alcohol?<br>Is there a simple way to reduce the CH2OH group to the CH3?<br>Something like protecting the NH2 and esterifying the OH group with p-toluenesulfonic acid chloride, which upon reduction with LiALH4 should leave a methyl group. What would happen if the unprotected NH2 was reacted to the sulfonamide and this was subjected to the LiAlH4 reduction?<br>Will a hydrolyzable N-S-bond be the consequence? Or if the amino alcohol was treated with SO2Cl2? Will it form a cyclic<br>product which upon reduction gives the aminoalkyl-chain?<br>Any bee with information on this? </td> <td> </td> </tr> <tr class="text_bg"> <td align="left" valign="bottom"><img src="../forum/images/left_bottom.gif" border="0" height="12" width="9"></td> <td valign="middle" align="center" colspan="7"> </td> <td align="right" valign="bottom"><img src="../forum/images/right_bottom.gif" border="0" height="12" width="9"></td> </tr> <tr class="page_bg"> <td colspan="9"> </td> </tr> <td align="left" valign="top" class="text_bg"> <img src="../forum/images/left_top.gif" border="0" height="12" width="9"></td> <td colspan="7"><a name="Post479094"></a><a name="last"></a></a> </td> <td align="right" valign="top"><img src="../forum/images/right_top.gif" border="0" height="12" width="9"></td> </tr> <tr class="text_bg"> <td rowspan="2"> </td> <td rowspan="2"> </td> <td valign="top" align="center" rowspan="2"> biotechdude<br> <i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br> <span title="Posting date">12-26-03 00:35</span><br> <span title="Link to this post by using the markup [479094]">No 479094</span><br> </td> <td rowspan="2"> </td> <td rowspan="2" width="1" class="vert_ruler"> <img src="../forum/images/hr.gif" border="0" width="1" height="1"> </td> <td rowspan="2"> </td> <td class="text_bg" align="left" valign="top"> <b title="The subject of this post">Phe - Does work; but dont know how</b> </td> <td class="text_bg" align="right" valign="top"> </td> <td> </td> </tr> <tr class="text_bg"> <td colspan="2" valign="top" align="left"> <br> Swix has heard of big-bees who use phenylalanine as their major precurser. They keep their methods secret..(doh!)<br><br>This doesn't directly help, but gives hope that there is a light at the end of a certain tunnel. <br><br>Swix wants to go down the AA tunnel soon but has no idea how. Perhaps other AA's contain the right side chains? What are the chains wanted/needed? Swix knows AA's well so me bee able to help... <br> <span title="The signature"><hr>No Fucking Idea</span> </td> <td> </td> </tr> <tr class="text_bg"> <td align="left" valign="bottom"><img src="../forum/images/left_bottom.gif" border="0" height="12" width="9"></td> <td valign="middle" align="center" colspan="7"> </td> <td align="right" valign="bottom"><img src="../forum/images/right_bottom.gif" border="0" height="12" width="9"></td> </tr> <tr class="page_bg"> <td colspan="9"> </td> </tr> </body> </html>