Synonym:N-α-Fmoc-L-asparticacidα-4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]-amino}benzylesterProperties:
RelatedCategories | AminoAcids&Derivatives,AsparticAcid,ChemicalBIOLOGy,ChemicalSynthesis,PeptideChemistry |
Description:
Backgroundinformation
Quasi-orthogonally-protectedAspderivative.
TheDmabgroupcanberemovedselectivelyinthepresenceoftBu-basedprotectinggroupsbytreatmentwith2%hydrazineinDMF[1],makingthisderivativeanextremelyusefultoolforthepreparationofcyclicpeptidesbyFmocSPPSorforlibrarysynthesis.
Occasionallysluggishcleavageoftheaminobenzylmoietyisobserved[2,3].Intheseinstances,washingthesupportwith20%DIPEAinDMF/water(9:1)[2]orHClindioxane[4]hasbeenfoundtobeefficacious.
Fortheon-resinsynthesisofside-chaintoside-chainlactambridgedpeptides,thecombinationofLys(ivDde)andAsp(ODmab)isparticularlyadvantageoussincebothside-chainscanbesimultaneouslyunmaskedinasinglestep.
Toavoidaspartimideformation,itisadvisabletoemployanHmb-orDmb-protectedderivativeforintroductionoftheprecedingresidue.
Forapplicationsofthisderivativeinthesynthesisofcyclicpeptides,seereferences[5-7].
Theproductnumberforthisproductwaspreviously04-12-1176.
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Safety:
Storageclass
10-13Otherliquidsandsolids