合成路线:The condensation of tert-butoxycarbonyl-L-alanine (I) with benzyl D-isoglutaminate (II) by means of N-hydroxysuccinimide (NOHS) and dicyclohexylcarbodiimide (DCC) gives the protected dipeptide (III),which is hydrogenated with H2 over Pd/C in methanol yielding tert-butoxycarbonyl-D-isoglutaminyl-L-alanine (IV).The condensation of (IV) with Nepsilon-(benzyloxycarbonyl)-L-lysine benzyl ester (V) by means of ethyl chloroformate and triethylamine affords the protected tripeptide (VI),which is treated with trifluoroacetic acid (TFA) to afford L-alanyl-D-isoglutaminyl-(Nepsilon-benzyloxycarbonyl)-L-lysine benzyl ester (VII).
合成路线:The condensation of (VII) with 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid (VIII) by means of NOHS and DCC as before gives the protected muramyl tripeptide (IX) ,which is treated with acetic acid yielding the partially protected compound (X).
合成路线:Hydrogenation of (X) with H2 over Pd/C in acetic acid affords Nalpha-(N-acetylmuramoyl-L-alanyl-D-isoglutaminyl)-L-lysine (XI),which is finally condensed with N-hydroxynorbornene-2,3-dicarboxyimide ester of stearic acid (XII) by means of N-methylmorpholine in DMF.
参考文献标题:MUROCTASIN
文献作者:Robinson,C.P.
参考来源:Drugs Fut 1989,14(5),432
合成路线:The condensation of tert-butoxycarbonyl-L-alanine (I) with benzyl D-isoglutaminate (II) by means of N-hydroxysuccinimide (NOHS) and dicyclohexylcarbodiimide (DCC) gives the protected dipeptide (III),which is hydrogenated with H2 over Pd/C in methanol yielding tert-butoxycarbonyl-D-isoglutaminyl-L-alanine (IV).The condensation of (IV) with Nepsilon-(benzyloxycarbonyl)-L-lysine benzyl ester (V) by means of ethyl chloroformate and triethylamine affords the protected tripeptide (VI),which is treated with trifluoroacetic acid (TFA) to afford L-alanyl-D-isoglutaminyl-(Nepsilon-benzyloxycarbonyl)-L-lysine benzyl ester (VII).
合成路线:The condensation of (VII) with 1-O-benzyl-4,6-O-benzylidene-N-acetylmuramic acid (VIII) by means of NOHS and DCC as before gives the protected muramyl tripeptide (IX) ,which is treated with acetic acid yielding the partially protected compound (X).
合成路线:Hydrogenation of (X) with H2 over Pd/C in acetic acid affords Nalpha-(N-acetylmuramoyl-L-alanyl-D-isoglutaminyl)-L-lysine (XI),which is finally condensed with N-hydroxynorbornene-2,3-dicarboxyimide ester of stearic acid (XII) by means of N-methylmorpholine in DMF.
参考文献标题:Chemical synthesis of N-acetylmuramyl peptides with partial structures of bacterial cell wall and their analogs in relation to immunoadjuvant activities.1976,49(2): 533-9
文献作者:Shiba,T.; Kusumoto,S.; Tarumi,Y.; Ikenaka,K.
参考来源:Bull Chem Soc Jpn 1976,49(2),533
产品链接: CAS No. 78113-36-7››