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Warning Text’?’ џ Warning Text џџџ%ŽXŽTableStyleMedium9PivotStyleLight16`…vISheet1… –Sheet2…œ—Sheet3ššЃЃŒССыќgqRef. #Resin TypeLoadingmmol/gVendorAmineConcn.mol/LSolventT/oCTimeMinsМWy/nAcidCouplingReagentYield%PurityOligo length InstrumentComments Rink amide Novabiochemprimary ReactionNMPrtnbammolDICDMFAapptec Apex 396benzyl Rapp Polymere2x15sygives 2o amide at this positiondomestic microwave 1kWTKKK primary alkyl20eqRink amide MBHA Fluka>95>909C-Met is cleaved orthogonally with CNBr cyanogen bromideKnorr amide MBHAConcnC-Cys to conjugate fluoresceinPS A-RAM macrobeads 500-560umNovasyn TG 90um0.2-0.3 0.48-0.51PS macrobeads 500umAmount1.5-31 to 2%Rainin 12-channel peptide synthesizer20 eqneat24 eq>987, 6tempo, hydroxyquinoline2-chlorotrityl resin2-chlorotrityl resin aryl aminecyclo-6fritted syringeTpyBOP/DIEA in DMF with 2.4umol/mL soln, of linear peptide o/n at rt for cyclization>85100mg heterocyclic 56-95ca0.2 mL phenylethyl DMF or DMSOJAdded 2 C-terminal AA residues to facilitate trouble-free Edman sequencingTentaGel 140-170 um MB NH26, 8)25mL peptide synthesis vessel (Chemglass)40-6060-90digital photolithographyRink amide MBHA 50mg, 37umol2x3070-8170-9025-7063-80*NB Scientific Innova 4400 incubator shakerGsee text for description. >30000 features within a 1.5cm2 area of glass3Illiad 2 robotic workstation, Charybdis InstrumentsRNZ>N-benzylguanidine sidechain is lost under cleavage conditions TentaGel HL12902, 75um750mg histamineautomated robot synthesizerTentaGel Rink amineTentaGel -NH2 280-320um20-12039-6950-9518-2458-72Automated peptide synthesizer@cleavable hydrophilic linker, halogen tag for tandem MS analysis Sasrin resin2-Chlorotrityl resin1.5-2.040-90C-terminal aldehydeC-terminal thiol5Ligation. DIC:bromoacetic acid 0.93:1.0 optimal ratio85-9555-95N-terminus conjugation heterocyclic NMP / DMF60-18045-9310 to 8771-9278-95cheterocyclic amines, anilines. Use of KI catalyst. Reduced haloacid concentration and reaction time35, 452x1560, 90"Zymark robotic library synthesizer"a-chiral pendant group side chainsDMSO50-99lipid amine - see text.novel coupling for DMPE lipid amine - see textMethods Enzymol. Review30x2%Symphony multiple peptide synthesizerRink amide AM RAM50 eq.90s30 eq.30sW10 hrs. vs 4-5 days for 5-mers. Reagent concns. Lower than Blackwell uW procedure (194)AM / FABAL MBHAamine with 1 eq. TEA DMSO / DMF60-80PP syringe with PE porous disk%DeClercq test for reaction completion Rink amide BAL resin5 eq.5 eq. 300x220 eq.20 eq. DCM10 eq.10 eq. 60x284-98SKaiser or deClercq tests for acylation; Chloranil or de Clercq tests for amination.DM F 1:1 DMF:DCM7Acylation & amination steps checked with chloranil test5 mL 1:2 DMF:DCM ca chlorideTEA180x290x2AB Rink amide-MBHA LL (low loading)1.3-1.724 eq. #C S Bio 036 autopeptide synthesizerAnaspec2,2,2-trifluoroethylamine90-120'ABI 433A automated peptide synthesizer Nspe 1,2-13C-ba>ca (2 eq.) used with KI catalyst for first submonomer addition NMP or DCM24 eq.200 eq. 1 mL44 eq.38-7612 to 17Aldehyde resin6 to 2432-91$C-substituted by reductive aminationHBnitroaromatic aminert 13-20bDeactivated nitroaromatic amines require 60oC for 60 mins for bromide displacement, uW synthesizerRink amide 100-200 meshdeactivated amines56-9352-69DATriazole monomer 0.25, 6.7 eq.H1o amine.HCl with 1 eq. DIEA. 180 mins for first amination displacement.Rink amide TentaGel25 eq. NMP or DMSO1 - 1.5 0.6, 15 eq. ba anhydride10 to 30Pierce fritted PP tubeAphosphoric and sulfonamide amine submonomers for water solubilityMBRink amide aminomethyl PSFmoc-N-R-Gly-OH3 eq. DIC / HOBt7 to 224Microwave assisted, 60oC coupling crucial to successMDamine with 1eq. TEA0.1 mL2 to 3890-98$sonication for displacement reactionneat or 1 or 2 neat or NMP30 - 180 6, 11, 16glycosylated by click reaction5.4-350.2mL or 0.25mLFdeR3 mL2.5mL600 uL68-80Glycosyl aminesRMJLFmoc synthesis8 to 12TentaGel S RAM26-37&ABI 433A automated peptide synthesizer Rink amide AMCSarcosine and N-propagylglycine monomers for glycosylated peptoidsWhatman 50 cellulose paperbromophenol blue testSPOT synthesis 2, 40 eq.0.25-2.552-9060-8500.6M HOBt inclusion dropped yield from 75% to 5% 1.0, 10 eq.12 hr 2.0, 20 eq.400 uL25-55/Advanced Chemtech 348-omega peptide synthesizer2 uL0.8 - 515x3 ba dnp ester15x210 to 5444-933, 6ABIMED AutoSpot RobotTentaGel S RAM 130um 180 or 240Aminomethyl PS resin 500-550 um MAMP resin ca chloride NaI catalystTHFpy?Merrifield, Alpha-methoxyphenyl resin. Addition of amine first except amine solutionsame as refs. 182, 195 umol/cm20.5-0.9Chemtech Advanced scale /umol1g, 5002g, 100060-70 100mg, 18 50, 100mg 160, 250 mg 210, 300 mg 75 mg, 56 50 mg, 37 23 mg, 10oxyethylGly-OHN-Fmoc, N-benzyl- Y, G with 1 eq. TEAa-amino acids K, R, 5 eq., 2.1 Amt/coupling0.05% Tween 20 NMP or water/ 0.6, 12 eq. 0.6, 13 eq. 0.3, 8 eq.(Protein Technologies Inc)&Symphony automated peptide synthesizer*Milestone MicroSYNTH multimodal microwave Pazo submonomer amine. Reductive debromination of N-bromoacetamide to N-acetamide50-merrlow yield for hydroxyquinoline submonomer amine due to steric effects. Ca used after heterocyclic amine addition. 100mg, 7242 eq.CEM Discover monomode microwave/CEM Discover monomode microwave 50mL R.B. flaskamine glass surface42; 43; 44; 4522; 4647; 4648, 19 50, 51, 5253, 5428, 33, 56, 37, 3858, 597, 83, 6875, 7623, 7780, 8189, 90, 91, 92 N. Sewald 29R. Volkmer-Engert 99 T. Rana 100 R. Rocchi 101H. Wenschuh 102, 103 K. Fukase 104M.C. Pirrung 105, 106D.S. Brown 107 Burgess 108NotesTK=Kodadek groupKK=Kirshenbaum groupRNZ=Zuckermann group(AM / FA = Messegeur and Albericio groupsAB=Barron groupHB=Blackwell groupDA=Appella groupMB=Bradley groupMD=Disney groupFdeR=Riccadris groupRMJL=Liskamp groupba=bromacetic acidca=chloroacetic acid6Table 1S. 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