870992-70-4

Basic information

• Product Name: Glycine, (4R)-1-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-L-prolyl-, phenylmethyl ester
• CAS NO: 870992-70-4
• Molecular Formula: C19H25FN2O5
• Molecular Weight: 380.416
• Mol File: 870992-70-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Glycine, (4R)-1-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-L-prolyl-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Glycine, (4R)-1-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-L-prolyl-, phenylmethyl ester(870992-70-4)
• EPA Substance Registry System: Glycine, (4R)-1-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-L-prolyl-, phenylmethyl ester(870992-70-4)

Safety Data

• Hazardous Substances Data: 870992-70-4(Hazardous Substances Data)

Upstream product

• 1738-76-7 glycine benzyl ester p-toluenesulfonic acid salt 
• 203866-14-2 (2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 587887-98-7 2-benzyl 1-(tert-butyl) (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate 
• 132622-90-3 (2S,4S)-2-benzyl 1-tert-butyl 4-hydroxypyrrolidine-1,2-dicarboxylate 

Downstream Products

• 870992-74-8 N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester 
• 870992-72-6 N-9-fluorenylmethoxycarbonyl-(2S,4S)-4-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester 

Relevant articles and documents

Stereoelectronic and steric effects in the collagen triple helix: Toward a code for strand association

Collagen is the most abundant protein in animals. The protein consists of a helix of three strands, each with sequence X-Y-Gly. Natural collagen is most stable when X is (2S)-proline (Pro) and Y is (2S,4R)-4-hydroxyproline (4R-Hyp). We had shown previously that triple helices in which X is (2S,4S)-4- fluoroproline (4S-Flp) or Y is (2S,4R)-4-fluoroproline (4R-Flp) display hyperstability. This hyperstability arises from stereoelectronic effects that preorganize the main-chain dihedral angles in the conformation found in the triple helix. Here, we report the synthesis of strands containing both 4S-Flp in the X-position and 4R-Flp in the Y-position. We find that these strands do not form a stable triple helix, presumably because of an unfavorable steric interaction between fluoro groups on adjacent strands. Density functional theory calculations indicate that (2S,3S)-3-fluoroproline (3S-Flp), like 4S-Flp, should preorganize the main chain properly for triple-helix formation but without a steric conflict. Synthetic strands containing 3S-Flp in the X-position and 4R-Flp in the Y-position do form a triple helix. This helix is, however, less stable than one with Pro in the X-position, presumably because of an unfavorable inductive effect that diminishes the strength of the interstrand 3S-FlpC=O...H-NGly hydrogen bond. Thus, other forces can counter the benefits derived from the proper preorganization. Although (Pro-Pro-Gly) 7 and (4S-Flp-4R-Flp-Gly)7 do not form stable homotrimeric helices, mixtures of these two peptides form stable heterotrimeric helices containing one (Pro-Pro-Gly)7 strand and two (4S-Flp-4R-Flp-Gly) 7 strands. This stoichiometry can be understood by considering the cross sections of the two possible heterotrimeric helices. This unexpected finding portends the development of a "code" for the self-assembly of determinate triple helices from two or three strands.