Summary
The condensation products obtained from 0.01M S-glycyl-N-acetyl-cysteamine at different pH's were investigated. The highest yields of diketo-piperazine (approx. 50%) were observed in phosphate buffers between pH 7.5 and 8.5. The highest yields of diglycine (46%), triglycine (10%) and tetraglycine (2%) were observed in carbonate buffers at pH 9.5. At pH 8.0, over 90% of the glycyl residues of 0.15M S-glycyl-N-acetylcysteamine were incorporated into condensation products, mainly DKP (60–70%). The yields of products from the condensation of S-glycyl-ethanethiol under similar conditions closely re-sembled those obtained with S-glycyl-N-acetylcysteamine.
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Abbreviations
- Boc-gly :
-
N-tert-butyloxycarbonylglycine
- Ac-cys :
-
N-acetylcysteine
- csa :
-
cysteamine
- Ac-csa :
-
N-acetylcysteamine
- DKP :
-
diketopiperazine
- (gly) 2 :
-
diglycine
- (gly) 3 :
-
triglycine
- (gly) 4 :
-
tetraglycine
- glySEt :
-
S-glycyl-ethanethiol
- glyS-(Ac-cys) :
-
S-glycyl-N-acetylcysteine
- glyS-(Ac-csa) :
-
S-glycyl-N-acetylcysteamine
- Boc-glyS-(Ac-cys) :
-
S-(Boc-glycyl)-N-acetylcysteine
- Boc-glyS-(Ac-csa) :
-
S-(Boc-glycyl)-N-acetylcysteamine
- Boc-glySEt :
-
S-(Boc-glycyl)-ethanethiol
- gly-bydrox :
-
glycine hydroxamate
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Weber, A.L., Orgel, L.E. The formation of peptides from glycine thioesters. J Mol Evol 13, 193–202 (1979). https://doi.org/10.1007/BF01739479
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DOI: https://doi.org/10.1007/BF01739479