51154-06-4

Usage

Biochem/physiol Actions

Boc-3,4-Dehydro-L-Proline is an N-terminal protected amino acid used in solid-phase peptide synthesis (SPPS) to make peptides containing 3,4-Dehydro-L-proline.

Upstream product

• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 51077-13-5 N-tert-Butyloxycarbonyl-3,4-dehydro-DL-prolin 
• 3395-35-5 DL-3,4-Dehydroproline 
• 34619-03-9 tert-butyldicarbonate 
• 74844-93-2 N-BOC-3,4-didehydro-(S)-proline methyl ester 
• 83548-46-3 (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate 
• 203866-16-4 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate 

Downstream Products

• 233675-29-1 (S)-2-((1S,2S)-1-Benzyloxycarbonyl-2-hydroxy-2-methyl-butylcarbamoyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 182291-43-6 tert-butyl {(tert-butoxycarbonyl)[(1R)-2-[(2S)-2-({[(6-cyano-3-pyridinyl)methyl]amino}carbonyl)-2,5-dihydro-1H-pyrrol-1-yl]-1-(cyclohexylmethyl)-2-oxoethyl]amino}acetate 
• 182291-44-7 [tert-butoxycarbonyl-(1-cyclohexylmethyl-2-oxo-2-{2-[(6-thiocarbamoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-ethyl)-amino]-acetic acid tert-butyl ester 
• 788801-45-6 [tert-butoxycarbonyl-(1-cyclohexylmethyl-2-{2-[(6-methylsulfanylcarbonimidoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-2-oxo-ethyl)-amino]-acetic acid tert-butyl ester 
• 865469-49-4 (S)-2-benzyl 1-tert-butyl 1H-pyrrole-1,2(2H,5H)-dicarboxylate 
• 79680-63-0 N-Tosyl-3,4-dehydro-L-prolin 
• 57849-99-7 N-Tosyl-3,4-epoxy-L-prolin-methylester 
• 53685-03-3 N-Tosyl-3,4-dehydro-L-prolin-methylester 
• 135837-63-7 3,4-dehydro-1-(9-fluorenylmethoxycarbonyl)-L-proline 
• 202477-61-0 C₁₈H₂₁N₃O₃ 
• 90731-76-3 BOC-ΔPro-Pro-γAbu-Phe-Gly-Pro-Phe-Arg 

Relevant academic research and scientific papers

Synthetic Marine Sponge Collagen by Late-Stage Dihydroxylation

Based on the observation that an increased substrate size is paralleled by an enhanced diastereoselectivity, a late-stage dihydroxylation protocol toward the 21mer CMP (collagen model peptide) Ac-(Pro-Hyp-Gly)3-Pro-Dyp-Gly-(Pro-Hyp-Gly)3-NH2 is presented. C3 and C4 hydroxylation have a converse effect on the triple-helical stability of collagen. Their combined influence on the melting temperature was studied by NMR spectroscopy.

METHOD FOR PRODUCING FLUORINATED PROLINE DERIVATIVE

Disclosed is a method for efficiently producing a high-purity fluorinated proline derivative with high yield. Specifically disclosed is a method for producing a compound represented by the general formula (2) below wherein a compound represented by the formula (1) below is reacted with a fluorination agent, and then chlorine, bromine, iodine, hypochlorous acid, hypochlorite, hypobromous acid, hypobromite or N-halogenosuccinimide is caused to act on the reaction product obtained by the preceding reaction and containing the compound represented by the general formula (2) below and a by-product for chemically changing the by-product. (1) (In the formula (1), R1 represents an unsubstituted or substituted alkyl group having 1-6 carbon atoms or the like; R2 represents an unsubstituted or substituted alkyl group having 1-6 carbon atoms or the like; and R3 represents a hydroxyl group or the like.) (2) (In the formula (2), R1 and R2 are as defined above.)

Synthesis of Two Naturally Occuring Diastereomeric Dihydroxyprolines: 2,3-trans-3,4-trans-3,4-Dihydroxy-L-proline and 2,3-cis-3,4-trans-3,4-Dihydroxy-L-proline

Starting from 2-pyrrolecarboxylic acid the N-Boc derivative 6 is resolved into its optically active constituents by crystalisation with R(+)-1-(4-nitrophenyl)ethaneamin.The N-tosyl-3,4-dehydro-L-proline methyl ester (L-7) derived from this is converted by