以L 苯丙氨酸为原料经还原反应得到氨基醇,再用Boc基团对中间体进行氨基保护得到(S) 3 苯基 2 叔丁氧羰基氨基 1 丙醇,甲磺酰化后与硫代乙酸钾在DMF中反应得到(S) 3 苯基 2 叔丁氧羰基氨基 1 丙硫醇乙酸酯,再脱除乙酰基后得到目标产物(S) 3 苯基 2 叔丁氧羰基氨基 1 丙硫醇(N Boc APT).分别应用红外光谱、核磁共振对中间体和目标化合物进行表征.同时,利用自组装技术将N Boc APT修饰于金电极表面,并测定其相关的电化学性能;此外,还将金纳米粒子组装在上述修饰电极上,并研究亚甲基蓝于该修饰电极的电化学行为.结果表明,金纳米粒子对该电极过程具有促进作用.
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 ~(1)HNMR. 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.
[1]HulstR,HeresH,PeterNCMW,etal.Synthesisandapplicationofnewchiralligandsfortheasymmetricboranereductionofprochiralketones[J].Tetrahedron:Asymmetry,1996,7(5):1373.
[2]FroelichO,BoninM,QuirionJC,etal.Diazaborolidines,anewclassofenantioselectiveorganoboroncatalyticagents[J].Tetrahedron:Asymmetry,1993,4(11):2335.
[3] HandrickGR,AtkinsonER,GranchelliFE,etal.Potentialantiradiationdrugs.Ⅱ.2 amino 1 alkanethiols,1amino 2 alkanethiols,2 thiazolines,and2 thiazoline 2 thiols[J],J.Med.Chem.,1965,8:762.
[4] MckennonMJ,MeyersAI,KarlheinzD,etal.AConvenientrductionofainoaidsandteirdrivatives[J].J.Org.Chem.,1993,58(13):3568.
[5] DaytonMA,BrownJC,StuttsKJ,etal.Faradaicelectrochemistryatmicrovoltammetricelectrodes[J].Anal.Chem.,1980,52:946.
[6] KaufmanFB,SchroederAH,EnglerEM,etal.IonandElectronTransportinStable,Electroactivetetrathiafulvalenepolymercoatedelectrodes[J].J.Am.Chem.Soc.,1980,102(2):483.
[7] WongSS,PorterMD.Originofthemultiplevoltammetricdesorptionwavesoflong chainalkanethiolatemonolayerschemisorbedonannealedgoldelectrodes[J].J.Electroanal.Chem.,2000,485:135.
[8] ZhaoFQ,ZengBCh,PangDW,VoltammetricstudyofmethyleneblueatthiolSAMs modifiedgoldelectrodes[J].Electroanalysis,2003,15(12):1060.
[9] SagaraT,KawamuraH,NakashimaN,etal.Electrodereactionofmethyleneblueatanalkanethiol modifiedgoldelectrodeascharacterizedbyelectroreflectancespectroscopy[J].Langmuir,1996,12:4253.
