Synthesis of (S)-3-Phenylpropane-2-tert-butoxycarbonylamino-1-thiol and its Electrochemical Behavior Self-assembled on Gold

Authors

Ru SUN, Department of Chemistry and Chemical Engineering, Suzhou University, Jiangsu 215006, China
Jian-feng GE, Department of Chemistry and Chemical Engineering, Suzhou University, Jiangsu 215006, China
Mei WANG, Department of Chemistry and Chemical Engineering, Suzhou University, Jiangsu 215006, China
Ren-ao GU, Department of Chemistry and Chemical Engineering, Suzhou University, Jiangsu 215006, ChinaFollow

Corresponding Author

Ren-ao GU(ragu@suda.edu.cn)

Abstract

The synthesis of (S)-3-Phenylpropane-2-tert-butoxycarbonylamino-1-thiol(N-Boc-APT) from L-phenylalanine was reported. L-Phenylalanine was reduced to the corresponding amino alcohol, protection of the amino group using tert-butyl pyrocarbonate gave (S)-2-tert-butoxycarbonylamino-3-phenylpropane-1-ol, which was then O-mesylated and treated with potassium thioacetate in DMF to give 3-phenylpropane-2-tert- butoxycarbonylamino-1-etylmercapto. After the acetyl group was removed with ammonia in alcohol, the desired target molecular was obtained. The structure of intermediate and target molecular was conformed by IR and ¹HNMR. We made N-Boc-APT self-assemble-modificated gold electrode and investigated its electrochemical behavior. The CV results of methylene blue on nano-Au/N-Boc-APT SAM/Au electrode showed that nano-Au could speed this electron transfer process.

Keywords

(S)-3-Phenylpropane-2-tert-butoxycarbonylamino-1-thiol, Asymmetric synthesis, Self-assembled, Electrochemistry, Gold nanoparticals, Methylene blue

DOI Link

https://doi.org/10.61558/2993-074X.1579

Publication Date

2004-08-28

Online Available Date

2004-08-28

Revised Date

2004-02-20

Received Date

2004-01-09

Recommended Citation

Ru SUN, Jian-feng GE, Mei WANG, Ren-ao GU. Synthesis of (S)-3-Phenylpropane-2-tert-butoxycarbonylamino-1-thiol and its Electrochemical Behavior Self-assembled on Gold[J]. Journal of Electrochemistry, 2004 , 10(3): 307-313.
DOI: 10.61558/2993-074X.1579
Available at: https://jelectrochem.xmu.edu.cn/journal/vol10/iss3/9