5617-01-6

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 6456-74-2 Glycine tert-butyl ester 
• 27532-96-3 glycine tert-butyl ester hydrochloride 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 

Downstream Products

• 83280-12-0 Z-Phe-Pro-Gly-OBu^t 
• 83280-14-2 {[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-acetic acid tert-butyl ester 
• 83704-72-7 Boc-Pro-Gly-Glu(Leu-Phe-Ala-NHNHZ)-Pro-Gly-O-t-Bu 
• 83704-71-6 phthalyl-Glu(Leu-Phe-Ala-NHNHZ)-Pro-Gly-O-t-Bu 
• 83704-81-8 ({(S)-1-[(S)-2-Amino-4-((S)-1-{(S)-1-[(S)-2-(N'-benzyloxycarbonyl-hydrazino)-1-methyl-2-oxo-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-butyryl]-pyrrolidine-2-carbonyl}-amino)-acetic acid tert-butyl ester 
• 83704-69-2 (S)-4-Benzyloxycarbonylamino-5-[(S)-2-(tert-butoxycarbonylmethyl-carbamoyl)-pyrrolidin-1-yl]-5-oxo-pentanoic acid benzyl ester 

Relevant academic research and scientific papers

Convenient synthesis of collagen-related tripeptides for segment condensation

Chromatography is a common step in the solution-phase synthesis of typical peptides, as well as peptide fragments for subsequent coupling on a solid support. Combining known reagents that form readily separable byproducts is shown to eliminate this step, which wastes time and other resources. Specifically, activating carboxyl groups with isobutyl chloroformate or as pentafluorophenyl esters and using N-methyl morpholine as a base enable chromatography-free synthetic routes in which peptide products are isolated from byproducts by facile evaporation, extraction, and trituration. This methodology was used to access tripeptides related to collagen, such as Fmoc-Pro-Pro-Gly-OH and Fmoc-Pro-Hyp(tBu)-Gly-OH, in a purity suitable for solid-phase segment condensation to form collagen mimetic peptides.