Factors Influencing the Acid Lability of Substituted Arylsulphonyl Arginine Protecting Groups
1994 ◽
Vol 49
(10)
◽
pp. 1425-1433
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Keyword(s):
AbstractThe kinetics of hydrolysis of new, NG-protected 2,4,6-triisopropylbenzene-sulphonyl (6). 4-methoxy-3,5-di-tert-butylbenzenesulphonyl (12) and phenanthrene-3-sulphonyl (17) Fmoc derivatives of L-arginine (1) in comparison with commercially available Fmoc-Arg(Mtr)-OH (Mtr = 4-methoxy-2,3,6-trimethyl-benzenesulphonyl (2)) are studies. The acid lability of the arylsulphonyl group is decreasing as follows Mtr > Tip > Mtbs > Phen. The effect of electron- donating alkyl groups as substituents in increasing the acid lability of the arylsulphonyl residue seems to be in the order of methyl > isopropyl > tert-butyl while the effect of extended derealization does not appreciably increase the acid lability.
1984 ◽
Vol 234
(1)
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pp. 82-88
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Keyword(s):
1966 ◽
Vol 88
(16)
◽
pp. 3808-3813
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1999 ◽
Vol 65
(18-19)
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pp. 2007-2010
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Keyword(s):
1971 ◽
Vol 36
(12)
◽
pp. 4115-4117
◽
1981 ◽
Vol 46
(5)
◽
pp. 1229-1236
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Keyword(s):