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Tetrahedron Letters

Volumn 32, Issue 51, 1991, Pages 7617-7620

Formation of peptide thioamides by use of Fmoc amino monothioacids and PyBOP.

(4) Høeg Jensen, Thomas a Havsteen Jakobsen, Mogens b Olsen, Carl Erik a Holm, Arne a

a UNIVERSITY OF COPENHAGEN (Denmark)

b UNIVERSITY OF COPENHAGEN (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0026316855 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(91)80549-L Document Type: Article

Times cited : (33)

References (25)

1
- 84918602970
- t, tert-butyl. Z, benzyloxycarbonyl. DMF, dimethylformamide. TFA, trifluoroacetic acid. DCC, dicyclohexylcarbodiimide. The use of ψ(CSNH) designates the presence of the thioamide function. PyBOP® and amino acid derivatives were purchased from Novabiochem, Switzerland. Unless otherwise indicated, all described amino acids are L-forms.

2
- 0000788606
- Review, Weinstein B., Marcel Dekker, New York
- (1983) Chemistry and Biochemistry of Amino Acids, Peptides and Proteins , vol.7 , pp. 267-357
- A.F.¹

3
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- and references therein.
- (1986) Tetrahedron , vol.42 , pp. 6555-6564
- Jensen¹ Senning²

4
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- and references therein.
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- (1990) Tetrahedron Letters , vol.31 , pp. 23-26
- Guziec¹ Wasmund²

6
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- (1985) Tetrahedron , vol.41 , pp. 5061-5087
- Cava¹ Levinson²

7
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- (1983) Tetrahedron Letters , vol.24 , pp. 3815-3818
- Lajoie¹ Lépine² Maziak³ Belleau⁴

8
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- (1989) Chem. Research (S) , pp. 155
- Guziec¹ Wasmund²

9
- 0041914939
- (1989) Chem. Research (M) , pp. 1301-1309
- Guziec¹ Wasmund²

10
- 0021056762
- (1983) Tetrahedron , vol.39 , pp. 3429-3435
- Thorsen¹ Yde² Pedersen³ Clausen⁴ Lawesson⁵

11
- 0010402992
- Aminosäure-thionester und Endothiopeptide
- (1960) Angewandte Chemie , vol.72 , pp. 268
- Reid¹ von der Emden²

12
- 37049088288
- Thioesters of amino acid derivatives as thioacylating agents in thiopeptide synthesis
- (1988) Journal of the Chemical Society, Perkin Transactions 1 , pp. 1051-1055
- Elmore¹ Guthrie² Kay³ Williams⁴

13
- 0003965863
- Weast R.C, Astle M.J., 63rd ed., CRC Press, Florida, (Bond strengths in diatomic molecules).
- (1982) Handbook of Chemistry & Physics , pp. F185-F194
- Kerr¹ Trotman-Dickenson²

14
- 36948999982
- (1987) Tetrahedron Letters , vol.28 , pp. 2171-2174
- Brown¹ Campbell² Chambers³ Walker⁴

15
- 84918600218
- The CSNH-group may under certain conditions undergo reaction with nucleophilic amines (see fx: Sauvé, G; Rao, V.S; Lajoie, G; and Belleau, B: Can. J. Chem. 1985, 63, 3089-3101). The commonly used Fmoc-deprotecting agent, piperidine, may however be substituted with non-nucleophilic DBU (Wade, J.D; Beford, J.; Sheppard, R.C; and Treagar, G.W: Peptide Research 1991, 4, 194-99).

16
- 0019629467
- (1981) Int. J. Peptide Protein Res. , vol.18 , pp. 383-392
- Yamashiro¹ Blake²

17
- 0025279990
- (1990) Int. J. Peptide Protein Res. , vol.35 , pp. 352-356
- Mitin¹ Zapevalova²

18
- 84918600832
- To be reported in detail elsewhere.

19
- 84918632547
- Fmoc-Gly-Phe-OEt prepared by standard method (DCC/HOBt). Fmoc-Gly-ψ(CSNH)-Phe-OEt prepared by use of Lawessons Reagent.

20
- 37049095054
- Studies on amino acids and peptides. Part 6. Methods for introducing thioamide bonds into the peptide backbone: synthesis of the four monothio analogues of leucine enkephalin
- (1984) Journal of the Chemical Society, Perkin Transactions 1 , pp. 785-798
- Clausen¹ Thorsen² Lawesson³ Spatola⁴

21
- 0021717544
- (1984) Int. J. Peptide Protein Res. , vol.24 , pp. 316-327
- Lajoie¹ Lépine² Lemaire³ Jolicoeur⁴ Aubé⁵ Turcotte⁶ Belleau⁷

22
- 84918642382
- Høeg-Jensen, T; Havsteen Jakobsen, M; Holm, A: Tetrahedron Letters. In press.

23
- 84918648766
- When activation of oxoacids is monitored, the starting signal disappears within a few minutes.

24
- 0010352326
- J.E Rivier, G.R. Marshall, ESCOM, Leiden
- (1990) Peptides. Proceedings of the 11 th American Peptide Symposium , pp. 885-888
- Coste¹ Dufour² Le-Nguyen³ Castro⁴

25
- 84918625188
- Also the facts, that both monothioacids and their corresponding disulfides are weakly acylating agents, may explain for the presence of oxopeptides in the crude products.

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