78804-97-4

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 67943-19-5 cis-1-acetyl-4-hydroxy-DL-proline-methyl ester 
• 5281-69-6 5-bromomethyl-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 49761-17-3 cis-4-hydroxyproline 
• 33996-33-7 cis-1-acetyl-4-hydroxy-DL-proline 
• 159912-52-4 (2S,4R)-N-acetyl-4-acetoxyproline methyl ester 
• 857479-57-3 5-bromomethyl-3-chloro-dihydro-furan-2-one 
• 854657-58-2 3-bromo-5-chloromethyl-dihydro-furan-2-one 
• 2584-72-7 3-chloro-5-chloromethyl-dihydro-furan-2-one 
• 66267-44-5 N-acetyl-cis-4-hydroxy-L-proline 
• 51-35-4 4R-4-hydroxyproline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 80-48-8 methyl p-toluene sulfonate 
• 67943-19-5 methyl (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylate 

Downstream Products

• 78854-29-2 (2S,4R)-1-Acetyl-4-benzylsulfanyl-pyrrolidine-2-carboxylic acid methyl ester 
• 78854-28-1 N-acetyl-4(R)-(benzylthio)pyrrolidine-2(S)-carboxylic acid 
• 618-28-0 trans-4-hydroxy-D,L-proline 
• 77449-96-8 cis-1-acetyl-4-(toluene-4-sulfonyloxy)-DL-proline 

Relevant academic research and scientific papers

Two prolines with a difference: contrasting stereoelectronic effects of 4R/S-aminoproline on triplex stability in collagen peptides [pro(X)-pro(Y)-Gly]n.

4R/S-Aminoprolines when present in the X-position of collagen peptide [pro(X)-pro(Y)-Gly]n exhibit pH- and stereochemistry-dependent effects on triplex stability.

Sulfinic Acids and Related Compounds. 13. Unsymmetrical Disulfides Based on Methyl 4-Mercaptobutanesulfinate and 4(S)- or 4(R)-Mercaptoprolines

In a study of disulfide-sulfinates containing prolylthio moieties epimeric at C-4, the OH group of N-acetylated 4(R)-hydroxy-2(S)-pyrrolidinecarboxylic acid ("trans-4-hydroxy-L-proline", 3) was converted to an epimeric SH group (11) by replacing a 4-O-tosyl group with PhCH2S (to give 5) and debenzylating.Reaction of 11 as the disodium salt with 1,2-dithiane 1,1-dioxide (2) replaced the H of the SH with S(CH2)4SO2Na to give a disulfide-sulfinate salt (9).Since 9 was unstable in solution, with conversion of disodium 4,4'-trithiobis(butanesulfinate) (22) to the diester 23 as a model, 9 was converted to the disulfide-sulfinic ester 10.Subsidiary peaks in the 13C NMR spectra of N-acetyl derivatives were shown to originate from rotamers.Similarly, the epimeric 4(S)-hydroxyproline (16) was converted to the 4(R)-mercaptoproline epimer (19) of 11, which was converted in turn to the disulfide-sulfinate epimer (21) of the sulfinic ester 10.The two disulfide-sulfinate esters 10 and 21 were stable under ambient conditions and began to disproportionate to the two symmetrical disulfides in refluxing ethylacetate in 1.5 (21) to ca. 7 h (10).The sulfinic esters 10, 21, and 23 seem likely to serve as biological precursors of sulfinate and thiolate salts, which may be usefull for several purposes.