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1
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0025997018
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Medicinal Chemistry in the Golden Age of Biology: Lessons from Steroid and Peptide Research
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Papers of particular interest, published within the annual period of review, have been highlighted as: of special interest of outstanding interest
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(1991)
Angew Chem
, vol.30
, pp. 1278-1301
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Hirschmann1
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5
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0026567563
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Site Specific Incorporation of Novel Backbone Structures into Proteins
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This is the first report of the successful introduction of conformationally constrained, non-coded amino acids into a protein using the suppressor tRNA strategy. Various replacements at position 82 of T4 lysozyme are reported. Replacements include α,α-dialkylated residues, N-alkyl amino acids and lactic acid.
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(1992)
Science
, vol.255
, pp. 197-200
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Ellman1
Mendel2
Schultz3
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6
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0026686436
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Total Chemical Synthesis of a d-Enzyme: the Enantiomers of HIV-1 Protease Show Demonstration of Reciprocal Chiral Substrate Specificity
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The preparation of an all-d analog of a 99-residue polypeptide illustrates the present state-of-the-art technology for assembling peptide chains on solid supports, and demonstrates the feasibility of incorporating non-coded residues by chemical synthesis.
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(1992)
Science
, vol.256
, pp. 1445-1448
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Milton1
Milton2
Kent3
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7
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0026525457
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Constructing Proteins by Dovetailing Unprotected Synthetic Peptides: Backbone-engineered HIV Protease
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The introduction of a thioester bond between residues Gly51 and Gly52 of the 99-residue protein HIV-1 protease is achieved by a chemical strategy involving the ligation of two large fragments prepared by total synthesis. The 1–51 peptide has a carboxy-terminal sulfur nucleophile, whereas the amino terminus of the 52–99 fragment bears an alkyl bromide function. Control of stereochemistry is facilitated by the choice of achiral glycine residues at the site of backbone engineering. This approach offers the possibility of introducing “fixed elements of 3D-structure” and “synthesis of hybrid protein-nonprotein macromoleculees”.
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(1992)
Science
, vol.256
, pp. 221-225
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Schnolzer1
Kent2
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9
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0026707702
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Helix Formation in Enzymatically Ligated Peptides as a Driving Force for the Synthetic Reaction: Example of α-Globin Semisynthetic Reaction
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(1992)
Biochemistry
, vol.31
, pp. 7249-7255
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Roy1
Khandke2
Manjula3
Acharya4
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12
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0025259162
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Nonprotein Amino Acid Furanomycin, Unlike Isoleucine in Chemical Structure, Is Charged to Isoleucine tRNA by Isoleucyl-tRNA Synthetase and Incorporated into Protein
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(1990)
J Biol Chem
, vol.265
, pp. 6931-6935
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Kohno1
Kohda2
Haruki3
Yokoyama4
Miyazawa5
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13
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0000932115
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A General and Efficient Route for Chemical Aminoacylation of Transfer RNAs
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The authors describe protocols which greatly simplify the preparation of tRNAs acylated with unusual amino acid residues. The aminoacylation of unprotected dinucleotide with an N-blocked amino acid residue, efficient ligation to tRNA and the subsequent photochemical unmasking of the amino group are important features of these methods.
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(1991)
J Am Chem Soc
, vol.113
, pp. 2722-2729
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Robertson1
Ellman2
Schultz3
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14
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0026082859
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Site-specific Incorporation of Non-natural Residues into Peptides: Effect of Residue Structure on Suppression and Translational Efficiencies
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Relative translation efficiencies for a series of 12 semi-synthetic acylated suppressor tRNAs are reported using a rapid assay procedure for determining suppression and translational efficiencies.
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(1991)
Tetrahedron
, vol.47
, pp. 2389-2400
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Bain1
Wacker2
Kuo3
Chamberlin4
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15
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0000237753
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Preparation of Chemically Misacylated Semisynthetic Non-sense Suppressor tRNAs Empolyed in Biosynthetic Incorporation of Non-natural Residues into Proteins
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Several synthetic routes for acylated tRNAs are described. Direct chemical synthesis is presented as an alternative to run-off transcription from a direct DNA template for tRNA synthesis. An l-3-iodotyrosine-charged suppressor tRNA is prepared by four procedures and an in vitro translation reaction is used to demonstrate similar suppression efficiencies in all cases.
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(1991)
J Org Chem
, vol.56
, pp. 4615-4625
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Bain1
Wacker2
Kuo3
Lyttle4
Chamberlin5
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21
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0025345233
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Structural Characteristics of α-Helical Peptide Molecules Containing Aib Residues
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(1990)
Biochemistry
, vol.29
, pp. 6747-6756
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Karle1
Balaram2
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22
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0000684607
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Folding Aggregation and Molecular Recognition in Peptides
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An overview of structural investigations of peptides, which contains a summary of crystallographic analyses of several Aib-containing peptide helices and discusses helix packing in crystals.
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(1992)
Acta Crystallographica Section B Structural Science
, vol.48
, pp. 341-356
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Karle1
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24
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0001263170
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Helix Construction Using α-Aminoisobutyryl Residues in a Modular Approach to Synthetic Protein Design. Conformational Properties of an Apolar Decapeptide in Two Different Crystal Forms and in Solution
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(1990)
Curr Sci
, vol.59
, pp. 875-885
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Karle1
Flippen-Anderson2
Uma3
Balaram4
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25
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84946381413
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The Design and Construction of Synthetic Protein Mimics
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This paper provides a summary of a design strategy that employs Aib residues and describes the synthesis of linked helix systems. The strong helix-nucleation properties of Aib are demonstrated by examples of the crystallographic characterization of several long peptides.
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(1992)
Pure and Applied Chemistry
, vol.64
, pp. 1061-1066
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Balaram1
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26
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0000403752
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Modular Design of Synthetic Protein Mimics. Crystal Structure of Two Seven-residue Helical Peptide Segments Linked by ε-Aminocaproic Acid
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The authors present an unambiguous conformational characterization of two peptide helices connected by a flexible chain-linking segment. A single centrally located. Aib residue suffices for helix nucleation in the heptapeptide fragments.
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(1991)
J Am Chem Soc
, vol.113
, pp. 3952-3956
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Karle1
Flippen-Anderson2
Sukumar3
Uma4
Balaram5
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41
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85015978398
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A Racemic Protein
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The preparation of all-d rubredoxin was motivated by a desire to grow centrosymmetric crystals of a racemic protein. However, the successful synthesis suggests that site-specific incorporation of d-residues by chemical methods should pose no problems in small proteins.
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(1992)
Journal of the American Chemical Society
, vol.114
, pp. 4002-4003
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Zawadzke1
Berg2
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42
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0026209013
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The Helical S Constant for Alanine in Water Derived from Template-nucleated Helices
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(1991)
Nature
, vol.352
, pp. 451-454
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Kemp1
Boyd2
Muendel3
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43
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0001411436
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1-OH)
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These two papers [42⊎,43⊎] describe a novel synthetic template for nucleating peptide helices, which is based on a modification of a Pro-Pro dipeptide.
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(1991)
J Org Chem
, vol.56
, pp. 6683-6697
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Kemp1
Curran2
Boyd3
Allen4
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44
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0025079448
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Synthesis and Conformational Analysis of Epindolidione Derived Peptides. Models for β-Sheet Formation
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(1990)
J Org Chem
, vol.55
, pp. 4650-4657
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Kemp1
Bowen2
Muendel3
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45
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0001334464
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Template-assembled Synthetic Proteins with Four Helix Bundle Topology. Total Chemical Synthesis and Conformational Studies
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A cyclic carrier molecule (decapeptide) bearing four lysine residues is used as a template for the covalent attachment of four putative helical (16-residue) peptides to the lysyl ε-amino groups. Limited circular-dichroism and NMR data demonstrate the helix-promoting effect of the template but do not unambiguously establish a four-helix-bundle topology.
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(1992)
J Am Chem Soc
, vol.114
, pp. 1463-1470
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Mutter1
Tuchscherer2
Miller3
Altmann4
Carey5
Wyss6
Labhardt7
Rivier8
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48
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0001141181
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A Convergent Approach to Protein Design. Metal Ion-assisted Spontaneous Self-assembly of a Polypeptide into a Triple-helix Bundle Protein
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This and the two preceding papers [46⊎,47⊎] address the common theme of using a metal-coordination site at the terminal ends of helical peptides to promote self assembly into oligomeric bundles. Detailed NMR or crystallographic characterizations of these synthetic ‘metalloproteins’ remain to be accomplished.
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(1992)
J Am Chem Soc
, vol.114
, pp. 825-831
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Ghadiri1
Soares2
Choi3
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49
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0026720252
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Probing Protein Stability with Unnatural Amino Acids
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This paper is a forerunner of things to come in the area of protein engineering with non-coded residues. T4 lysozyme is the model and position 133 is probed with a variety of replacements to examine packing, solvation and side-chain conformational entropy effects on stability. Two ‘non-coded mutants’ with marginally higher thermal stabilities are obtained.
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(1992)
Science
, vol.256
, pp. 1798-1802
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Mendel1
Ellman2
Chang3
Veenstra4
Kollman5
Schultz6
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50
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0000064374
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General Approach to the Synthesis of Short α-Helical Peptides
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A higher homolog of cysteine featuring the insertion of three additional methylene groups into the side chain, which is derived by chemical synthesis from lysine, disulfide bridges the i and i + 7 residues in potentially helical peptides (where i represents residue number from the amino terminus). Disulfide crosslinking enhances peptide helicity.
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(1991)
J Am Chem Soc
, vol.113
, pp. 9391-9392
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Jackson1
King2
Chmielewski3
Singh4
Schultz5
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51
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34447493365
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Sequential Site-directed Mutagenesis and Chemical Modification to Convert the Active Site Agrinine 292 of Aspartate Aminotransferase to Homoarginine
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This homologation of Arg292 is based on an initial site-specific mutation to lysine followed by chemical guanidination with O-methylisourea. Although modification occurs at several lysine residues, guanidinated enzymes often possess the same activity and are stable.
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(1992)
Journal of the American Chemical Society
, vol.114
, pp. 3567-3568
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White1
Kirsch2
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