Carbonate Handle Modified Wang Resin and Its Function†

doi:10.7503/cjcu20180548

Abstract

Abstract:

Because of the carbonate structure is removed by nucleophilic agents easily, methyl chloroformate was used to modify Wang resin, and the condensation efficiency of modified Wang resin with the first amino acid was studied. The results showed the condensation efficiency of the modified resin to 20 kinds of Fmoc amino acids could run up to 70%. In order to increase the condensation efficiency of the modified resin with the Fmoc amino acids achieving larger side chain groups, the degree of resin substitution was reduced and the reaction time was prolonged. In order to prove the protected side chain group would not be damaged under cleavage conditions of the modified Wang resin, three model peptides were resigned and synthesized, and cleaved by 3-pyridinecarboxaldehyde sulfonium salt. The results showed that the peptides with side chain fully protected could be obtained by using the modified Wang resin, and could also be preliminary applied to the synthesis of long-chain peptides.

Key words: Wang resin modification, Carbonate handle, Fmoc protected amino acid, Side chain full protective peptide

CLC Number:

O629.7

TrendMD:

ZHANG Ye,WU Weihui,ZONG Liang,DONG Junjun. Carbonate Handle Modified Wang Resin and Its Function^†[J]. Chem. J. Chinese Universities, 2019, 40(3): 462.

Figures/Tables 4

References 20

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Concentration/(mmol·L^-1)	Abs.	Concentration/(mmol·L^-1)	Abs.
0.0100	0.149	0.0600	0.672
0.0200	0.296	0.0700	0.777
0.0300	0.392	0.0800	0.872
0.0400	0.471	0.0900	0.985
0.0500	0.568	0.1000	1.051

Concentration/(mmol·L^-1)	Abs.	Concentration/(mmol·L^-1)	Abs.
0.0100	0.149	0.0600	0.672
0.0200	0.296	0.0700	0.777
0.0300	0.392	0.0800	0.872
0.0400	0.471	0.0900	0.985
0.0500	0.568	0.1000	1.051

Amino acid	Connection rate(%)	Amino acid	Connection rate(%)
Fmoc-Val-OH	93.2	Fmoc-Thr(tBu)-OH	84.9
Fmoc-pro-OH	89.1	Fmoc-Asn(Trt)-OH	77.0
Fmoc-Leu-OH	92.0	Fmoc-Trp(Boc)-OH	80.3
Fmoc-Ile-OH	92.3	Fmoc-Asp(otBu)-OH	84.2
Fmoc-Met-OH	90.5	Fmoc-Tyr(tBu)-OH	82.1
Fmoc-Phe-OH	88.7	Fmoc-Glu(otBu)-OH	81.9
Fmoc-Ala-OH	94.0	Fmoc-Cys(Trt)-OH	78.5
Fmoc-Gly-OH	95.3	Fmoc-Gln(Trt)-OH	75.3
Fmoc-Arg(Pbf)-OH	65.0	Fmoc-His(Trt)-OH	70.2
Fmoc-Lys(Boc)-OH	80.3	Fmoc-Ser(tBu)-OH	86.2

Amino acid	Connection rate(%)	Amino acid	Connection rate(%)
Fmoc-Val-OH	93.2	Fmoc-Thr(tBu)-OH	84.9
Fmoc-pro-OH	89.1	Fmoc-Asn(Trt)-OH	77.0
Fmoc-Leu-OH	92.0	Fmoc-Trp(Boc)-OH	80.3
Fmoc-Ile-OH	92.3	Fmoc-Asp(otBu)-OH	84.2
Fmoc-Met-OH	90.5	Fmoc-Tyr(tBu)-OH	82.1
Fmoc-Phe-OH	88.7	Fmoc-Glu(otBu)-OH	81.9
Fmoc-Ala-OH	94.0	Fmoc-Cys(Trt)-OH	78.5
Fmoc-Gly-OH	95.3	Fmoc-Gln(Trt)-OH	75.3
Fmoc-Arg(Pbf)-OH	65.0	Fmoc-His(Trt)-OH	70.2
Fmoc-Lys(Boc)-OH	80.3	Fmoc-Ser(tBu)-OH	86.2

Substitution degree/(mmol·g^-1)	Yield(%)	Reaction time/h	Yield(%)
1.06	65.6	2	65.0
0.84	70.8	3	72.1
0.43	72.3	4	71.4
0.22	72.0	5	71.8