In:
Israel Journal of Chemistry, Wiley, Vol. 12, No. 1-2 ( 1974-01), p. 79-85
Abstract:
The relative first‐order rates of deprotection of N ∈ ‐benzyloxycarbonyllysine in 2%, 10%, and 50% trifluoroacetic acid in dichloromethane at 20° are 1, 50, and 1000, respectively. The N ∈ ‐2‐chlorobenzyloxycarbonyl group is at least 60 times more stable than the N ∈ ‐benzyloxycarbonyl group under solid‐phase conditions, because no branched peptides ( 〈 0.2 mole%) were formed during synthesis of decalysylvaline using N α‐ tert ‐butyloxycarbonyl‐N ∈ ‐2‐chlorobenzyloxycarbonyllysine. Since O‐2‐chlorobenzylserine, N im ‐tosylhistidine, N im ‐2,4‐dinitrophenylhistidine and S‐4‐methylbenzylcysteine were completely stable in 50% trifluoroacetic acid–dichloromethane for over 200 h, these side‐chain protecting groups should be suitable for the solid‐phase synthesis of large peptides.
Type of Medium:
Online Resource
ISSN:
0021-2148
,
1869-5868
DOI:
10.1002/ijch.v12:1-2
DOI:
10.1002/ijch.197400009
Language:
English
Publisher:
Wiley
Publication Date:
1974
detail.hit.zdb_id:
2066481-3
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