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t-Boc amino acid chiral separation

Posted: Thu Nov 29, 2007 4:44 pm
by gseres
I am intend to separate t-BOC amino acid enantiomers, namely t-BOC cycloheptyl glycin enantiomers. I want to buy for tis purpose a new generation Beta-cyclodextrin bonded hydroxypropyl ether based Cyclobond 2000 HP-RSP column. According to Astec manufacturer's application broschure, it seems to be more stable and better selective than old Cyclobond 2000 RSP one, but this information material doesn't contain any t-BOC amino acid application. But this application is very familiar to old one. I think it probable to resolve t-BOC AAs on the new column, because the chiral selector is the same. I want to assure.
Have anybody a knowledge or practice to answer this question?
Dr. Gábor Seres
Senior Scientific Advisor
IVAX Drug Research Institute Ltd.
Quality Control Department
Phone: 36 1 399 33 00 ext. 81-89
gabor.seres@idri.hu

Posted: Mon Dec 03, 2007 8:25 pm
by JA
Hi,

Convenient thread timing, I just today began work on a project which, in part, requires separation of D and L stereoisomers of BOC-cyclohexylglycine (CAS 70491-05-3 and 109183-71-3, respectively).

So far I have the LC conditions down, but have found the following issue with ELS detection - a strong dependence of response and % area quantitation with column temperature.

Assuming similar behaviour of your compounds, for separation with Rs > 3.5 in under 10 mins you could consider the following:

Chiralcel OJ (or OJ-H) 250 x 4.6 mm
95:5:0.1 n-Hexane/IPA/AcOH
1.0 ml/min (30°C, see above)
k' (BOC-L-Chg-OH) ~ 0.65
k' (BOC-D-Chg-OH) ~ 1.02
Rs > 3.5

I just noticed I completely skipped your question :oops:

The answer is probably, but why don't you call the Astec rep and find out?

Regards