41446-04-2

Upstream product

• 3160-59-6 N-Cbz-L-Isoleucine 
• 543-27-1 isobutyl chloroformate 
• 73-32-5 L-isoleucine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 75816-40-9 N^α-benzyloxycarbonyl-L-hemilanthionyl-L-isoleucyl-L-seryl-L-leucine t-butyl ester L-hemilanthionine α'-methyl ester hydrochloride 
• 75816-44-3 L-hemilanthionyl-L-isoleucyl-L-seryl-L-leucyl-L-hemilanthionine α'-methyl ester picrate 
• 75816-52-3 (S)-2-[(S)-2-((2S,3S)-2-{(S)-2-Benzyloxycarbonylamino-3-[(R)-2-methoxycarbonyl-2-(trityl-amino)-ethylsulfanyl]-propionylamino}-3-methyl-pentanoylamino)-3-(diphenoxy-phosphoryloxy)-propionylamino]-4-methyl-pentanoic acid 
• 75832-13-2 (S)-2-[(S)-2-{(2S,3S)-2-[(S)-3-((R)-2-Amino-2-methoxycarbonyl-ethylsulfanyl)-2-benzyloxycarbonylamino-propionylamino]-3-methyl-pentanoylamino}-3-(diphenoxy-phosphoryloxy)-propionylamino]-4-methyl-pentanoic acid; hydrochloride 
• 75816-65-8 (S)-2-[(S)-2-((2S,3S)-2-{(S)-2-Benzyloxycarbonylamino-3-[(R)-2-methoxycarbonyl-2-(trityl-amino)-ethylsulfanyl]-propionylamino}-3-methyl-pentanoylamino)-3-(diphenoxy-phosphoryloxy)-propionylamino]-4-methyl-pentanoic acid tert-butyl ester 
• 75816-38-5 N^α-benzyloxycarbonyl-L-hemilanthionyl-L-isoleucyl-L-seryl-L-leucine t-butyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester 
• 75816-38-5 N^α-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyl-L-seryl-L-leucine t-butyl ester N^α'-trityl-L-hemilanthionine α'-methyl ester 
• 75816-58-9 Ile-Ser(Dpp)-Leu 
• 75816-64-7 Z-Ile-Ser(Dpp)-Leu-OBu^t 
• 75816-41-0 N^α-benzyloxycarbonyl-L-hemilanthionyl-L-isoleucyl-L-seryl-L-leucine L-hemilanthionine α'-methyl ester hydrochloride 
• 75816-42-1 N^α-benzyloxycarbonyl-L-hemilanthionyl-L-isoleucyl-L-seryl-L-leucyl-L-hemilanthionine α'-methyl ester 
• 75816-45-4 (S)-2-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-methanesulfonyloxy-propionylamino]-4-methyl-pentanoic acid tert-butyl ester 
• 1027083-91-5 [(1S,2S)-1-(5,6-Dihydro-pyrazin-2-yl)-2-methyl-butyl]-carbamic acid benzyl ester 
• 268747-19-9 [(1S,2S)-2-Methyl-1-(2-oxo-acetyl)-butyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Aza-Wittig rearrangement of N,N-dipropargylic α-amino alkyllithiums: Periselectivity and steric course

The aza-Wittig rearrangement of enantio-defined N,N-dipropargylic α-amino alkyllithiums, generated by tin-lithium exchange, are shown to afford [1,2]- and/or [2,3]-rearrangement products. Both aza-Wittig rearrangements proceed predominantly with inversion of configuration at the Li-bearing carbon terminus.

Enantiopure N-protected α-amino glyoxals 1. Synthesis from α-amino acids and some condensation reactions with amines

A series of N-protected α-ammo diazoketones has been prepared from L-amino acids and dipeptides and used as precursors in the synthesis of novel N-protected α-amino glyoxals via oxidation with distilled dimethyldioxirane (DMD) in acetone. The glyoxals have been converted, without purification, into enantiopure imines, pyrazines, quinoxalines, and pyrido[2,3-b]pyrazines via condensation with the appropriate amine or diamine. The molecular structure of the pyrido[2,3-b]pyrazine derived from N-Cbz-L-phenylalanine has been determined by X-ray analysis.

Peptidyl and azapeptidyl methylketones as substrate analog inhibitors of papin and cathepsin B

Peptidyl methylketones containing Phe, Tyr, Tyr(I), Tyr(I2), Leu and Ile in P2 were synthesized and tested as substrate analog revesible of papain and bovine spleen cathepsin B.The most effective cathepsin B inhibitor contained Tyr(I2) and displayed an inhibition constant of 4.7 μM at pH 6.8 and 25 deg C, while Leu or Ile gave practically inert analogs.Replacement of the amino acids in P2 with the analogues α-azaamino acids, as well as the glycine in P1 with α-azaglycine, led to complete loss of inhibiting activity.Introducing alkoxy substituents at themethyl adjacent to the ketone group generally resulted in more effective inhibitors, with inhibition constants in the micromolar range for both papin and cathepsin B. - Keywords: enzyme inhibiting activity; cysteine proptease; slow binding; peptidyl methylketone; azapeptidyl methylketone; papain; cathepsin B

Lanthionine Chemistry. Part 5. Synthesis of Cyclic Non-symmetrical Lanthionyl Peptides

The synthesis of a protected fragment of the antibiotic nisin, specifically Nα-benzyloxycarbonyl-D-hemilanthionyl-L-isoleucyldehydroalanyl-L-leucyl-L-hemilanthionine α'-methyl ester (B) and of its analogue Nα-benzyloxycarbonyl-L-hemi