102013-10-5

Upstream product

• 57653-38-0 N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 77345-53-0 (2S,4S)-N-1-(benzyloxycarbonyl)-4-(p-toluenesulfonyloxy)proline methyl ester 
• 197079-48-4 trans-N-(Benzyloxycarbonyl)-4-hydroxy-L-proline 
• 2232-08-8 N-tosylimidazole 
• 51-35-4 4R-4-hydroxyproline 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 86965-82-4 trans-4-(toluene-4-sulfonyloxy)-proline 
• 756846-17-0 (4R)-N-benzyloxycarbonyl-4-(4-toluenesulfonyloxy)-L-prolyl chloride 
• 376585-19-2 5-[1-benzyloxycarbonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-1-tert-butyloxycarbonyl-pyrrolidine-2-carboxylic acid methyl ester 
• 376585-21-6 2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid methyl ester 
• 376585-22-7 2-oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0(3,7)]tridecane-12-benzyloxycarbonyl-4-carboxylic acid tert-butyl ester 
• 376585-20-5 5-[1-benzyloxycarbonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonyl]-mercaptomethyl-pyrrolidine-2-carboxylic acid methyl ester 
• 727727-10-8 (1S,4S,7S,10S)-2-Oxo-9-thia-3,12-diaza-tricyclo[8.2.1.0^3,7]tridecane-4,12-dicarboxylic acid 12-benzyl ester 
• 83624-61-7 trans-4-methylsulfanyl-L-proline 
• 105996-14-3 N-(Bromoethyl)-4-tosyloxy-L-proline ethyl ester hydrobromide 
• 105996-15-4 N-(Hydroxyethylaminoethyl)-4-tosyloxy-L-proline ethyl ester 
• 105996-13-2 N-(Hydroxyethyl)-4-tosyloxy-L-proline ethyl ester 

Relevant academic research and scientific papers

A inhibiting DPP-IV compounds and intermediates

Provided are compounds as presented in formulas IA or IB or pharmaceutically acceptable salts thereof, the preparation method therefor, and uses thereof. Also provided are the intermediates of the compounds and the preparation method therefor. The compounds of the present invention can effectively inhibit DPP-IV activity. Compared to the commercial available medicine, Januvia, compound 1 exhibits strong inhibition against DPP4, but has lower activity inhibition against other DPP family members (DPP2, DPP8, and DPP9). Hence the compound of the present invention can not only effectively inhibit DPP4 from exhibiting medicinal activity, but also lower the activity inhibition against other members of the DPP family, reduce toxic side effect, and have better medicinal safety.

Novel asymmetric approach to proline-derived spiro-β-lactams

We describe a novel asymmetric approach using Staudinger chemistry to proline-derived spiro-β-lactams. A chiral group at C-4 of the acid chloride of proline directs the stereoselectivity of Staudinger chemistry and later is sacrificed to obtain optically active 5.4-spiro-β-lactams. The scope, limitations, and mechanistic rationale for the observed results of Staudinger Chemistry of the acid chloride of 4-alkyl(aryl)sulfonyloxy-L-proline with imines are also discussed.

Optimal N-caps for N-terminal helical templates: Effects of changes in H-bonding efficiency and charge

A family of efficient helix-initiating N-terminal caps X-Hel is introduced that expand the scope and versatility of the previously reported reporting conformational template Ac-Hel, (Kemp, D. S.; Allen, T. J.; Oslick, S. J. Am. Chem. Soc. 1995, 117, 6641-6657) and a working principle for predicting cap performance is described, based on structurally specific intramolecular hydrogen bond formation. Replacement of the N-acetyl by urethane, urea, or sulfonamide generated less efficient polypeptide helix inducers. The N-formyl cap is found to be equivalent to the N-acetyl and may provide more convenient quantitative helix reporting properties. Anionic N-caps derived from the series X = -O2C-(CH2)n-CO, 0 ≤ n ≤ 3, are superior to N-acetyl, as are N-acylglycyl and N-acyl-β-aspartyl. The latter pair of caps permit introduction of the X-Hel functionality within a polypeptide chain, allowing control of helicity of a peptide sub-sequence. Applications of these capping functions are discussed. This work has been focused primarily on immediate practical goals directed toward enhancing the maximum helicity of isolated short to medium-sized peptides in aqueous solution, but its developing concepts and working hypotheses are likely to significantly enhance our understanding at a chemical level of the protein folding problem.

HALOGENATED SUBSTITUTED MERCAPTOACYLAMINO ACIDS

New halogen substituted mercaptoacylamino acids which have the general formula STR1 and basic salts thereof are useful as hypotensive agents.