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Volumn 34, Issue 31, 1993, Pages 4885-4888

Solid-phase synthesis of O-palmitoylated peptides

Author keywords

[No Author keywords available]

Indexed keywords

FATTY ACID DERIVATIVE;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; PRIORITY JOURNAL; PROTEIN SYNTHESIS;

EID: 0027301315 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)74037-8 Document Type: Article

Times cited : (14)

References (27)

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9
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- Williams¹ Narcessian² Andersen³ Waller⁴ Taylor⁵ Lazenby⁶ Hinton⁷ Koeppe⁸

10
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- Alternative Strategies for the Fmoc Solid-Phase Synthesis ofO4-Phospho-L-tyrosine-Containing Peptides
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- Kitas¹ Knorr² Trzeciak³ Bannwarth⁴

11
- 0003834870
- Review, G.A. Grant, W.H. Freeman and Co, New York
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- Fields¹ Tian² Barany³

12
- 84918751136
- 2O, di-tertiary-butyl dicarbonate; Bzl, benzyl; DCM, dichloromethane; DIPCDI, N,N-diisopropylcarbodiimide; DMAP, 4-dimethylaminopyridine; DMF, N,N-dimethylformamide; DNPA, 2,4-dinitrophenyl-5-L-alanine amide; ES-MS, electrospray mass spectrometry; FAB-MS, fast atom bombardment mass spectrometry; FDAA, 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide, Fmoc, 9-fluorenylmethoxycarbonyl; HOBt, 1-hydroxybenzotriazole; HPLC, high-performance liquid chromatography; Pal, palmitoyl; Pye, pyridylethyl; tBu, tertiary-butyl; TFA, trifluoroacetic acid; TLC, thin layer chromatography. All amino acids are of the L-configuration unless otherwise designated.

13
- 0026051772
- Gramicidin K has been synthesized by acylation of the ethanolamidated C-terminus of gramicidin A with palmitic acid, dicyclohexylcarbodiimide, and 4-pyrolidinopyridine in benzene, This solution-phase procedure is not applicable for peptides in general, however, as gramicidin A has only the ethanolamine hydroxyl group available for acylation.
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- Vogt¹ Killian² Demel³ De Kruijff⁴

16
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- A brief (10 min) piperidine-DMF (1:4) treatment was used for Fmoc-Asp(OtBu)-Thr-Rink resin to minimize aspartimide formation. Based on prior studies of aspartimide formation from Asp(OtBu)-Gly (ref. 12a) and Asp(OBzl)-Thr (ref. 12b) sequences, ≈ 1.4% aspartimide formation was predicted for our sequence.

17
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19
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- 2O (9:11) containing 0.1% TFA. Variation in retention times is due to relative sample loadings and column condition.

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- 2O containing 0.1% TFA and B was acetonitrile containing 0.1% TFA.

22
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23
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24
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27
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