In:
Israel Journal of Chemistry, Wiley, Vol. 17, No. 4 ( 1978-01), p. 243-247
Abstract:
The Boc‐aminoacyl‐OCH 2 ‐Pam‐ derivative of Kel F‐g‐styrene resin has been synthesized by a chemically unambiguous route. Direct amidoalkylation of the unsubstituted resin followed by hydrazinolysis gave the aminomethyl‐resin. The loaded resin was obtained by reaction with a Boc‐aminoacyl‐OCH 2 ‐phenylacetic acid and DCC. The stability of this resin derivative towards acidolysis in trifluoroacetic acid was determined. Only 0.01–0.02 mol% loss of chains will occur in a single deprotection cycle in solid phase peptide synthesis. The peptidyl‐ and aminoacyl‐OCH 2 ‐Pam‐(Kel F‐g‐styrene) resins were cleaved with anhydrous HF‐anisole at 0°C in near‐quantitative yield. Simultaneous syntheses of the model peptide Leu‐Ala‐Gly‐Val on this resin and on Val‐OCH 2 ‐Pam‐poly(styrene‐ co ‐1% divinylbenzene) resin gave the same low levels of byproducts. No ( 〈 0.1%) intersite aminolysis was observed on treatment of Leu‐Ala‐Gly‐Val‐OCH 〈 2 ‐Pam‐(Kel F‐g‐styrene) resin with 5% diisopropylethylamine in dichloromethane for 22 h.
Type of Medium:
Online Resource
ISSN:
0021-2148
,
1869-5868
DOI:
10.1002/ijch.197800043
Language:
English
Publisher:
Wiley
Publication Date:
1978
detail.hit.zdb_id:
2066481-3
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