72086-86-3

Usage

InChI:InChI=1/C16H29N3O6/c1-9(18-14(23)25-15(3,4)5)11(20)19(10(2)12(21)24-8)13(22)16(6,7)17/h9-10H,17H2,1-8H3,(H,18,23)/t9-,10-/m0/s1

Upstream product

• 72086-77-2 (tert-butyloxycarbonyl)-L-alanyl-α-aminoisobutyric acid methyl ester 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 10065-72-2 L-Alanine methyl ester 
• 72095-04-6 Boc-Ala-Aib-OH 
• 79118-33-5 Boc-Ala-Aib-OBzl 
• 109208-68-6 Boc-Ala-O-COO-isoBu 
• 15761-38-3 L-N-Boc-Ala 

Downstream Products

• 79083-85-5 Boc-L-Ala-₂-Glu(OBzl)-₂-Ala-OMe 
• 82954-83-4 H-L-Glu(OBzl)-L-Ala-Aib-Ala-Aib-Ala-OMe*CF₃COOH 
• 82954-81-2 Boc-L-Glu(OBzl)-Ala-₂-OMe 
• 70904-77-7 Z-Aib-Pro-Aib-Ala-Aib-Ala-OMe 
• 79205-75-7 Z-Aib-Pro-Aib-Ala-Aib-Ala-OH 
• 76487-60-0 Z-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-Leu-Aib-OMe 
• 76487-61-1 Z-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-Leu-Aib-OH 
• 184100-04-7 (S)-3-(2-{(S)-2-[2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-2-methyl-propionylamino]-propionylamino}-2-methyl-propionylamino)-N-{(S)-1-[1-((S)-1-methoxycarbonyl-ethylcarbamoyl)-1-methyl-ethylcarbamoyl]-ethyl}-succinamic acid benzyl ester 
• 184100-02-5 (S)-3-tert-Butoxycarbonylamino-N-{(S)-1-[1-((S)-1-methoxycarbonyl-ethylcarbamoyl)-1-methyl-ethylcarbamoyl]-ethyl}-succinamic acid benzyl ester 

Relevant academic research and scientific papers

STUDIES ON AMINO ACIDS AND PEPTIDES XII. SYNTHESIS OF THIATED ANALOGUES OF Boc-S-Ala-Aib-S-Ala-OMe AND Ac-S-Ala-Aib-S-Ala-OMe

The two model peptides Boc-S-Ala-Aib-S-Ala-OMe (1a) and Ac-S-Ala-Aib-S-Ala-OMe (1b) and their monothiated analogues Boc-S(R)-AlaΨ(CSNH)-Aib-S-Ala-OMe (3a), Boc-S-Ala-AibΨ(CSNH)-S-Ala-OMe (4a), AcΨ(CSNH)-S-Ala-Aib-S-Ala-OMe (2b), Ac-S-Ala-AibΨ(CSNH)-S-Ala-OMe (4b), and the dithiated Boc-S-AlaΨ(CSNH)-AibΨ(CSNH)-S-Ala-OMe (5a) are synthesized.Peptide 3a was obtained from the coupling of HCl*H-S-Ala-OMe to S-2-(1-tert-butoxycarbonylamino)ethyl-4,4-dimethyl-1,3-thiazol-5(4H)-one (11).The thioamide analogues 4a (together with 5a) and 2b were obtained by regioselective thiation of the respective model peptides 1a and 1b using 2,4-bis(4-methylphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, Lawesson's Reagent (LR).Deprotection of the Boc group of 4a, followed by acetylation of the product, afforded 4b.The magnetic nonequivalence of the gem-methyl groups of Aib is discussed.

SOLUTION CONFORMATIONS OF PENTA AND HEPTAPEPTIDES CONTAINING REPETITIVE α-AMINOISOBUTYRYL-L-ALANYL AND α-AMINOISOBUTYRYL-L-VALYL SEQUENCES

The presence of folded solution conformations in the peptides Boc-Ala-(Aib-Ala)2-OMe, Boc-Val-(Aib-Val)2-OMe, Boc-Ala-(Aib-Ala)3-OMe and Boc-Val-(Aib-Val)3-OMe has been established by 270 MHz 1H NMR.Intramolecularly H-bonded NH groups have been identified using temperature and solvent dependence of NH chemical shifts and paramagnetic radical induced broadening of NH resonances.Both pentapeptides adopt 310 helical conformations possessing 3 intramolecular H-bonds in CDCl3 and (CD3)2SO.The heptapeptides favour helical structures with 5 H-bonds in CDCl3.In(CD3)2SO only 4 H-bonds are readily detected.

The effect of a peptide helix macrodipole on the pKa of an asp side chain carboxylate

A study of the effect of a helix dipole on the pKa of a side chain functional group has been undertaken to determine the magnitude of these electrostatic effects in the absence of interfering influences from a protein matrix. Three helical pept

SOLUTION PHASE SYNTHESIS OF ALAMETHICIN I

The total synthesis of alamethicin I by solution phase methods is reported.