Synthesis and 12-helical secondary structure of beta-peptides containing (2R,3R)-aminoproline.

نویسندگان

  • Emilie A Porter
  • Xifang Wang
  • Margaret A Schmitt
  • Samuel H Gellman
چکیده

[structure: see text] (2R,3R)-Aminoproline, a pyrrolidine-based beta-amino acid, was synthesized and incorporated into hexa-beta-peptide 4. This residue confers water solubility when the ring nitrogen is protonated and allows for 12-helix formation in aqueous solution. Circular dichroism spectra display the 12-helical signature, and 12-helical structure was confirmed by 2D NMR analysis.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Secondary Structure Effects on the Acidity of Histidine and Lysine-Based Peptides Model; A Theoretical Study

     In this study, the effect of the secondary structure of the protein on the acid strength of three structures of random (R), alpha helix (α) and beta sheet (b) were investigated theoretically. These structures are related to the cationic amino acids of histidine and lysine in the polypeptide chain of eight-glycine residue. Computational methods at the HF, B3LYP, X3LYP and M05-2X levels in t...

متن کامل

Enantioselective Synthesis of a (+)-(2R, 3R)-1,4-Benzodioxane-7-carbaldehyde Derivative, a Key Intermediate in the Total Synthesis of Haedoxan Analogs.

(+)-(2R,3R)-7-Formyl-6-methoxy-2-methoxymethyl-3- (3,4-methylenedioxyphenyl)-2,3-dihydro-1,4-benzodioxin (2), a key building block for the total synthesis of haedoxan A, was synthesized from (4R)-4-(phenylmethyl)-2-oxazolidinone (3) in ten steps with a 12% overall yield.

متن کامل

Characterization of a (2R,3R)-2,3-Butanediol Dehydrogenase from Rhodococcus erythropolis WZ010.

The gene encoding a (2R,3R)-2,3-butanediol dehydrogenase from Rhodococcus erythropolis WZ010 (ReBDH) was over-expressed in Escherichia coli and the resulting recombinant ReBDH was successfully purified by Ni-affinity chromatography. The purified ReBDH in the native form was found to exist as a monomer with a calculated subunit size of 37180, belonging to the family of the zinc-containing alcoho...

متن کامل

Analogues of Methyl Y)-Ribo- and D-Arafo/io-furanosides Having Phosphorus in the Anomeric Position+

Recently, we have completed syntheses of (2R , 3R , 4R)-3-C-(hydroxym ethyl)-2-m ethoxy-2-oxo-l,2oxaphospholane-3,4-diol as well as of (2R , 3R , 4S, 5R )and (2S, 3R , 4S, SR ^^'-O -benzylid en e-S-O (terr-butyldimethylsilyl)-5-C-(hydroxymethyl)-2m ethoxy-2-oxo-l,2-oxaphospholane-3,4-diol which were considered as analogues of C-2 branched-chainD-threose and D-lyxose containing phosphorus in the...

متن کامل

A practical route to partially protected pyrrolidines as precursors for the stereoselective synthesis of alexines.

Either 3-O-benzoyl- (2a) or 3-O-benzyl-1,2-O-isopropylidene-beta-D-fructopyranose (2b) were regioselectively O-benzylated at C-4 to give 4a and 4b, respectively, which were transformed into 5-azido-3-O-benzoyl-4-O-benzyl- (6a) and 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-alpha-L-sorbopyranose (6b) by nucleophilic displacement of the corresponding 5-O-mesyl derivatives 5a and 5b by s...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic letters

دوره 4 19  شماره 

صفحات  -

تاریخ انتشار 2002