Properties, metabolisms, and applications of l-proline analogues

Applied Microbiology and Biotechnology

Volumn 97, Issue 15, 2013, Pages 6623-6634

  Bach, Thi Mai Hoa ^a   Takagi, Hiroshi ^b  

^a GRADUATE UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Viet Nam)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

cis 4 Hydroxy d proline; cis 4 Hydroxy l proline; Hydroxyprolines; l Azetidine 2 carboxylic acid; l Proline analogues; l Proline cis 4 hydroxylase; N acetyl cis 4 hydroxy l proline; N acetyltransferase Mpr1; trans 4 Hydroxy d proline; trans 4 Hydroxy l proline

Indexed keywords

CIS-4-HYDROXY-D-PROLINE; CIS-4-HYDROXY-L-PROLINE; L-PROLINE; N ACETYLS; N-ACETYLTRANSFERASES; TRANS-4-HYDROXY-D-PROLINE; TRANS-4-HYDROXY-L-PROLINE;

CARBOXYLIC ACIDS; INDUSTRIAL APPLICATIONS; INDUSTRIAL RESEARCH; MAMMALS; METABOLISM; ORGANIC COMPOUNDS; TISSUE CULTURE;

HYDROXYPROLINE;

ALLOHYDROXYPROLINE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; AZETIDINE 2 CARBOXYLIC ACID; BENZODIAZEPINE DERIVATIVE; CASPOFUNGIN; CELL MEMBRANE PROTEIN; CYTOTOXIC AGENT; HYDROXYPROLINE; MACROGOL; NITROGEN; OXACEPROL; PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE; PROLINE DERIVATIVE; RETRONECINE; UNCLASSIFIED DRUG;

AMINO ACID; EUKARYOTE; INDUSTRIAL PRODUCTION; METABOLISM; PROKARYOTE; PROTEIN; RESEARCH AND DEVELOPMENT; TOXIC MATERIAL;

ACINETOBACTER BAUMANNII; AMANITA; AMANITA PHALLOIDES; ANTINEOPLASTIC ACTIVITY; ARTHROPATHY; BEET; BIOTRANSFORMATION; CELL DEATH; CELL METABOLISM; CONVALLARIA; DETOXIFICATION; DRUG SYNTHESIS; ENDOPLASMIC RETICULUM STRESS; ENTERITIS; ENZYME MECHANISM; GLIOCLADIUM; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS; HYDROXYLATION; LILIACEAE; MYTILUS EDULIS; NEGATIVE FEEDBACK; NONHUMAN; OSTEOARTHRITIS; OSTEOPOROSIS; OXIDATIVE STRESS; PANTOEA AGGLOMERANS; PHYSICAL CHEMISTRY; PROTEIN EXPRESSION; PROTEIN METABOLISM; PSEUDOMONAS; PSORIASIS; REVIEW; SANTALUM ALBUM; STREPTOMYCES; STREPTOMYCES ANTIBIOTICUS; UNSPECIFIED SIDE EFFECT; VIRUS REPLICATION; WOUND;

AZETIDINECARBOXYLIC ACID; BIOTRANSFORMATION; PROLINE;

CONVALLARIA; CONVALLARIA MAJALIS; EUKARYOTA; HUMULUS; MAMMALIA; PROKARYOTA;

EID: 84880511790     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-5022-7     Document Type: Review

References (126)

1. Adam E, Norton IL (1964) Purification and properties of inducible hydroxyproline 2-epimerase from Pseudomonas. J Biol Chem 239:1525-1535
2. Adams E, Leonard F (1980) Metabolism of proline and the hydroxyproline. Ann Rev Biochem 49:1005-1061
3. Ananthan J, Goldberg AL, Voellmy R (1986) Abnormal proteins serve as eukaryotic stress signals and trigger the activation of heat shock genes. Science 232:522-524
4. Aoki M, Suto K, Komatsu M, Kamimura A, Morishita K, Yamasaki M, Takao T (2012) Increasing effect of an oral intake l-hydroxyproline on the soluble collagen content of skin and collagen fragments in rat serum. Biosci Biotechnol Biochem 76:1242-1244
5. Bach TMH, Hara R, Kino K, Ohtsu I, Yoshida N, Takagi H (2013) Microbial production of N-acetyl cis-4-hydroxy-l-proline by coexpression of the Rhizobium l-proline cis-4-hydroxylase and the yeast N-acetyltransferase Mpr1. Appl Microbiol Biotechnol 97:247-257
6. Bontoux MC, Gelo-Pujic M (2006) Microbial screening in hydroxylation of l-proline. Tetrahedron Lett 47:9073-9076
7. Buku A, Wieland T, Bodenmuller H, Faulstich H (1980) Amaniamide, a new toxin of Amanita virosa mushrooms. Experientia 36:33-34
8. Carpenter JF, Crowe JH (1988) Modes of stabilization of a protein by organic solutes during desiccation. Cryobiology 25:459-470
9. Chekler ELP, Butera JA, Di L, Swillo RE, Morgan GA, Rossman EI, Huselton C, Larsen BD, Hennan JK (2009) Discovery of a class of potent gap-junction modifiers as novel antiarrhythmic agents. Bioorg Med Chem Lett 19:4551-4554
10. Chen C, Dickman MB (2005) Proline suppresses apoptosis in the fungal pathogen Colletotrichum trifolii. Proc Natl Acad Sci USA 102:3459-3464
11. Clare BW, Ferro V, Skelton BW, Stick RV, White AH (1993) Approaches to synthesis of retronecine from some pyrrolidine precursors. Aust J Chem 46:805-824
12. Csonka LN (1981) Proline over-production results in enhanced osmotolerance in Salmonella typhimurium. Mol Gen Genet 182:82-86
13. Csonka LN, Gelvin SB, Goodner BW, Orser CS, Siemieniak D, Slightom JL (1988) Nucleotide sequence of a mutation in the proB gene of Escherichia coli that confers proline overproduction and enhanced tolerance to osmotic stress. Gene 64:199-205
14. Csonka LN, Hanson AD (1991) Prokaryotic osmoregulation: genetics and physiology. Annu Rev Microbiol 45:569-606
15. Delauney AJ, Verma DPS (1993) Proline biosynthesis and osmoregulation in plants. Plant J 4:215-223
16. Dho JC, Fleet GWJ, Peach JM, Prout K, Smith PW (1986) Synthesis of 2R,3S,4R-dihydroxyproline from d-rionolactone. Tetrahedron Lett 27:5203-5204
17. Dicosimo R, Fager SK, Gavagan JE (2001) Producing diastereomers of 4-hydroxyproline using 4-hp epimerase from Serratia marcescens or Acinetobacter baumanni. United Stated Patent 6204050
18. Du X, Takagi H (2005) N-acetyltransferase Mpr1 confers freeze tolerance on Saccharomyces cerevisiae by reducing reactive oxygen species. J Bacteriol 138:391-397
19. Du X, Takagi H (2007) N-Acetyltransferase Mpr1 confers ethanol tolerance on Saccharomyces cerevisiae by reducing reactive oxygen species. Appl Microbiol Biotechnol 75:1343-1351
20. Eldridge CF, Bunge RP, Bunge MB (1988) Effect of cis-4-hydroxy-l-proline, an inhibitor of Schwann cell differentiation, on the secretion of collagens and noncollagenous protein by Schwann cells. Exp Cell Res 174:491-501
21. Elijah A, Leonard F (1980) Metabolism of proline and the hydroxyproline. Ann Rev Biochem 49:1005-1061
22. Faulstich H, Buku A, Bodenmuller H, Wieland T (1980) Virotoxins: actin-binding cyclic peptides of Amanita virosa mushrooms. Biochemistry 19:3334-3343
23. Fleet GW, Karpas A, Dwek RA, Fellows LE, Tyms AS, Petursson S, Namgoong SK, Ramsden NG, Smith PW, Son JC (1988) Inhibition of HIV replication by amino-sugar derivative. FEBS Lett 237:128-132
24. Fowden L (1956) Azetidine-2-carboxylic acid: a new cyclic imino acid occurring in plants. Biochem J 64:323-332
25. Fowden L, Richmond MH (1963) Replacement of proline by azetidine-2-carboxylic acid during biosynthesis of protein. Biochim Biophys Acta 71:459-461
26. Fujii K, Ikai Y, Oka H, Suzuki M, Harada K (1997) A non empirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: combination of Marfey's method with mass spectrometry and its practical application. Anal Chem 69:5146-5151
27. Gray DO (1972) trans-4-Hydroxymethyl-d-proline from Eriobotrya japonica. Phytochemistry 11:751-756
28. Gross C, Felsheim R, Wackett LP (2008) Genes and enzymes of azetidine-2-carboxylate metabolism: detoxification and assimilation of an antibiotic. J Bacteriol 190:4859-4864
29. Haitani Y, Nakata M, Sasaki T, Uchida A, Takagi H (2009) Engineering of the yeast ubiquitin ligase Rsp5: isolation of a new variant that induces constitutive inactivation of the general amino acid permease Gap1. FEMS Yeast Res 9:73-86
30. Hara R, Kino K (2009) Characterization of novel 2-oxoglutarate dependent dioxygenases converting l-proline to cis-4-hydroxy-l-proline. Biochem Biophys Res Commun 379:882-886
31. Harris CM, Schneider MJ, Ungemach FS, Hill JE, Harris TM (1988) Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola: metabolism of 1-hydroindolizidines. J Am Chem Soc 110:940-949
32. Hashizume J, Hattori S, Igarashi M, Akamatsu Y (2004) Tripropeptin E, a new tripropeptin group antibiotic produced by Lysobacter sp. BMK333-48F3. J Antibiot 57:394-403
33. Hibi T, Yamamoto H, Nakamura G, Takagi H (2009) Crystallization and preliminary crystallographic analysis of N-acetyltransferase Mpr1 from Saccharomyces cerevisiae. Acta Crystallogr Sect F: Struct Biol Cryst Commun 65(Pt 2):169-172
34. Hill RK, Rhee SW, Isono K, Crout DHG, Suhadolnik RJ (1981) Stereospecificity of the enzymatic dehydrogenation in the biosynthesis of 3-ethylidene-l-azetidine-2-carboxylic acid from isoleucine by Streptomyces cacaoi. Biochemistry 20:7040-7042
35. Hoa BTM, Hibi T, Nasuno R, Matsuo G, Sasano Y, Takagi H (2012) Production of N-acetyl cis-4-hydroxy-l-proline by the yeast N-acetyltransferase Mpr1. J Biosci Bioeng 114:160-165
36. 1-pyrroline-5-carboxylate synthetase results in increased proline accumulation and protection of plants from osmotic stress. Plant Physiol 122:1129-1136
37. Hosoya T, Matsuoka T, Serizawa N, Furuya K (1995) Two morphological groups derived from Clonostachys cylindrospora and their relationship to trans-4-l-proline productivity. Mycoscience 36:193-197
38. Hottiger T, De Virgilio C, Hall MN, Boller T, Wiemken A (1994) The role of trehalose synthesis for the acquisition of thermotolerance in yeast. II. Physiological concentrations of trehalose increase the thermal stability of proteins in vitro. Eur J Biochem 219:187-193
39. Ignatova Z, Gierasch LM (2006) Inhibition of protein aggregation in vitro and in vivo by a natural osmoprotectant. Proc Natl Acad Sci USA 103:13357-13361
40. Iinoya K, Kotani T, Sasano Y, Takagi H (2009) Engineering of the yeast antioxidant enzyme Mpr1 for enhanced activity and stability. Biotechnol Bioeng 103:341-352
41. Ishchuk OP, Abbas CA, Sibirny AA (2010) Heterologous expression of Saccharomyces cerevisiae MPR1 gene confers tolerance to ethanol and l-azetidine-2-carboxylic acid in Hansenula polymorpha. J Ind Microbiol Biotechnol 37:213-218
42. Johnston RM, Chu LN, Liu M, Goldberg SL, Goswami A, Patel RN (2009) Hydroxylation of l-proline to cis-3-hydroxy-l-proline by recombinant Escherichia coli expressing a synthetic l-proline-3-hydroxylase gene. Enzym Micro Tech 45:484-490
43. Katz E, Kamal F, Mason K (1979) Biosynthesis of trans-4-hydroxy-l-proline by Streptomyces griseoviridus. J Biol Chem 254:6684-6690
44. Katz ED, Prockop DJ, Udenfriend S (1962) Precursors of the hydroxyproline and ketoproline in actinomycin. J Biol Chem 237:1585-1588
45. Kaul S, Sharma SS, Mehta IK (2008) Free radical scavenging potential of l-proline: evidence from in vitro assays. Amino Acids 34:315-320
46. Kelley PM, Schlesinger MJ (1978) In vitro synthesis of heat-shock proteins by mRNAs from chicken embryo fibroblasts. Cell 15:1277-1286
47. Kimura Y, Nakamori S, Takagi H (2002) Polymorphism of the MPR1 gene required for toxic proline analogue resistance in the Saccharomyces cerevisiae complex species. Yeast 19:1437-1445
48. Klohs WD, Steinkampf RW, Wicha MS, Mertus AE, Tunac JB, Leopold WR (1985) Collagen-production inhibitors evaluated as antitumor argents. J Natl Cancer Inst 75:353-359
49. Koehn F, Longley RE, Reed J (1992) Microcolins A and B new immunosuppressive peptides from the blue-green alga Lyngbya majuscula. J Nat Prod 55:613-619
50. Krishnan N, Dickman MB, Becker DF (2008) Proline modulates the intracellular redox environment and protects mammalian cells against oxidative stress. Free Radic Biol Med 44:671-681
51. Kuttan R, Radhakrishnan AN (1970) The biosynthesis of cis-4-hydroxy-l-proline in sandal (Santalum album L.). Biochem J 117:1015-1017
52. Lasko PF, Brandriss MC (1981) Proline transport in Saccharomyces cerevisiae. J Bacteriol 148:241-247
53. Laursen R (1992) Reflection on the structure of mussel adhesive protein. Results Probl Cell Differentiation 19:52-72
54. Lawrence CC, Sobey WJ, Field RA, Baldwin JE, Schofield CJ (1996) Purification and initial characterization of proline 4-hydroxylase from Streptomyces griseoviridus P8648: a 2-oxoacid, ferrous-dependent dioxygenase involved in etamycin biosynthesis. Biochem J 313:185-191
55. Leete E (1964) The biosynthesis of azetidine-2-carboxylic acid. J Am Chem Soc 86:3162
56. Leete E, Louters LL, Rao H, Prakash S (1986) Biosynthesis of azetidine-2-carboxylic acid in Convallaria majalis: studies with N-15 labelled precursors. Phytochemistry 25:2753-2758
57. Lubec B, Mallingher R, Radner W, Vycudilik W, Hausler J, Lubec G (1993) Cis 3 hydroxyproline reduces glomerular basement membrane thickness and collagen type IV synthesis in diabetic rats. Amino Acids 4:249-254
58. Matsuoka T, Serizawa N, Hosoya T, Furuya K (1994) Isolated cultures of microorganism of Clonostachys cylindrospora, Gliocladium and Nectria gliocladioides. US Patent 5,407,826
59. Matsuoka T, Furuya K, Serizawa N (1995) Fermentation production of cis-4-hydroxy-l-proline by Helicocerus oryzae and Acrocylindrium oryzae. Biosci Biotechnol Biochem 58:1747-1748
60. Mizzen LA, Welch WJ (1988) Characterization of the thermotolerant cell. I. effects of protein synthesis activity and the regulation of heat-shock protein 70 expression. J Cell Biol 106:1105-1116
61. Mohanty AP, Matysik J (2001) Effect of proline on the production of single oxygen. Amino Acids 21:195-200
62. Mori H, Shibasaki T, Yano K, Ozaki A (1997) Purification and cloning of a proline 3-hydroxylase, a novel enzyme which hydroxylate free l-proline to cis-3-hydroxy-l-proline. J Bacteriol 179:5677-5683
63. Mori H, Shibasaki Y, Uozaki K, Ochiai K, Ozaki A (1996) Detection of novel proline 3-hydroxylase activities in Streptomyces and Bacillus spp. by regio- and stereospecific hydroxylation of l-proline. Appl Environ Microbiol 62:1903-1907
64. Morita Y, Nakamori S, Takagi H (2003) l-Proline accumulation and freeze tolerance of Saccharomyces cerevisiae are caused by a mutation in the PRO1 gene encoding γ-glutamyl kinase. Appl Environ Microbiol 69:212-219
65. Mueller C, Emmrich J, Jaster R, Braun D, Liebe S, Sparmann G (2006) cis-Hydroxyproline-induced inhibition of pancreatic cancer cell growth is mediated by endoplasmic reticulum stress. World J Gastroenterol 12:1569-1576
66. Mulzer J, Meier A (1996) Total synthesis of cis- and trans-3-hydroxy-d- proline and (+)-detoxin. J Org Chem 61:566-572
67. Nakajima T, Volcani BE (1969) 3,4-Dihydroxyproline: a new amino acid in diatom cell walls. Science 164:1400-1401
68. Navnath BK, Kasture VM, Dhavale DD (2010) Total synthesis of natural cis-3-hydroxy-l-proline from d-glucose. Tetrahdron Lett 51:6745-6747
69. Nishimura A, Kawahara N, Takagi H (2013) The flavoprotein Tah18-dependent NO synthesis confers high-temperature stress tolerance on yeast cells. Biochem Biophys Res Commun 430:137-143
70. Nishimura A, Kotani T, Sasano Y, Takagi H (2010) An antioxidative mechanism mediated by the yeast N-acetyltransferase Mpr1: oxidative stress-induced arginine synthesis and its physiological role. FEMS Yeast Res 10:687-698
71. 1-pyrroline-5-carboxylate directly inhibits the mitochondrial respiration in budding yeast. FEBS Lett 586:2411-2416
72. Nomura M, Nakamori S, Takagi H (2003) Characterization of novel acetyltransferases found in budding and fission yeasts that detoxify a proline analogue, azetidine-2-carboxylic acid. J Biochem 133:67-74
73. Nomura M, Takagi H (2004) Role of the yeast acetyltransferase Mpr1 in oxidative stress: regulation of oxygen reactive species caused by a toxic proline catabolism intermediate. Proc Natl Acad Sci USA 101:12616-12621
74. Ogawa-Mitsuhashi K, Sagane K, Kuromitsu J, Takagi H, Tsukahara K (2009) MPR1 as a novel selection marker in Saccharomyces cerevisiae. Yeast 26:587-593
75. Olszewski U, Ellinger A, Zeillinger R, Baumgartner G, Hamilton G (2008) Involvement of 14-3-3sigma in cytotoxicity of cis-4-hydroxy-l-proline (CHP) against epithelial tumor cell lines. FEBS Proceedings, C2-152.
76. Omura S, Fujimoto T, Otoguro K, Matsuzaki K, Moriguchi R, Tanaka J, Sasaki Y (1991) Lactacystin a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells. J Antibiot 44:113-116
77. Onishi MY, Okumura R, Okamoto R, Ishikura T (1984) Proline hydroxylation by cell free extract of a streptomycete. Biochem Biophys Res Commun 120:45-51
78. Peterson PJ, Fowden L (1963) Different specificities of proline-activating enzymes from some plant species. Nature 200:148-151
79. Petersen L, Hughes D, Hughes R, DiMichele L, Salmon P, Connors N (2001) Effects of amino acid and trace element supplementation on the pneumocandin production by Glarea lozoyensis: impact on titer, analogues levels, and the identification of new analogues of pneumocandin B0. J Ind Microbiol Biotechnol 26:216-221
80. Piatnitski CEL, Butera JA, Di L, Swillo RE, Morgan GA, Rossman EI, Huselton C, Larsen BD, Hennan JK (2009) Discovery of a class of potent gap-junction modifiers as novel antiarrhythmic agents. Bioorg Med Chem Lett 19:4551-4555
81. Poiani GJ, Riley DJ, Fox JD, Kemnitzer JE, Gean KF, Kohn J (1994) Conjugates of cis-4-hydroxy-l-proline and poly(PEG-Lys), a water soluble poly(ether urethane): synthesis and evaluation of antifibrotic effects in vitro and in vivo. Bioconjugate Chem 5:621-630
82. Puska M, Yli-Urpo A, Vallittu P, Airola K (2005) Synthesis and characterization of polyamide of trans-4-hydroxy-l-proline used as porogen filler in acrylic bone cement. J Biomater Appl 19:287-301
83. Rajendrakumar CSV, Suryanarayana T, Reddy AR (1997) DNA helix destabilization by proline and betaine: possible role in the salinity tolerance process. FEBS Lett 410:201-205
84. Reese LM, Cutler KO, Deutch CE (1996) Sensitivity of Escherichia coli to proline analogues during osmotic stress and anaerobiosis. Lett Appl Microbiol 22:202-205
85. Remuzon P (1996) Trans-4-hydroxy-l-proline, a useful and versatile chiral starting block. Tetrahedron 52:13803-13835
86. Riley DJ, Berg RA, Edelman NH, Prockop DJ (1980) Prevention of collagen deposition following pulmonary oxygen toxicity in the rat by cis-4-hydroxy-l-proline. J Clin Invest 65:643-651
87. Rosenbloom J, Prockop D (1971) Incorporation of cis-hydroxyproline into protocollagen and collagen. J Biol Chem 246:1549-1555
88. Rowe RC, Sheskey PJ, Weller PJ (2003) Polyethylene glycols. In: Rowe RC, Sheskey PJ, Weller PJ (eds) Handbook of pharmaceutical excipients, 6th edn. Pharmaceutical Press, London, pp 517-522
89. Rubenstein E (2000) Biologic effects of and clinical disorders caused by nonprotein amino acids. Medicine 79:80-89
90. Rubenstein E, Zhou H, Krasinska KM, Chien A, Becker CH (2006) Azetidine-2-carboxylic acid in garden beets (Beta vulgaris). Phytochemistry 67:898-903
91. Rudd MT, McCauley JA, Butcher JW, Romano JJ, McIntyre CJ, Nguyen KT, Gilbert KJ, Bush KJ, Holloway MK, Swestock J, Wan BL, Carroll SS, DiMuzio JM, Graham DJ, Ludmerer SW, Stahlhut MW, Fandozzi CM, Trainor N, Olsen DB, Vacca JP, Liverton NJ (2011) Discovery of MK-1220: a macrocyclic inhibitor of hepatitis C virus NS3/4A protease with improved preclinical plasma exposure. ACS Med Chem Lett 2:207-212
92. Rudolph AS, Crowe JH (1985) Membrane stabilization during freezing: the role of two natural cryoprotectants, trehalose and proline. Cryobiology 22:367-377
93. Samuel D, Kumar TKS, Ganesh G, Jayaraman G, Yang PW, Chang MM, Trivedi VD, Wang SL, Hwang KC, Chang DK, Yu C (2000) Proline inhibits aggregation during protein refolding. Protein Sci 9:344-352
94. Sasano Y, Haitani Y, Hashida K, Ohtsu I, Shima J, Takagi H (2012) Enhancement of the proline and nitric oxide synthetic pathway improves fermentation ability under multiple baking-associated stress conditions in industrial baker's yeast. Microb Cell Fact 11:40. doi: 10.1186/1475-2859-11-40
95. Sasano Y, Takahashi S, Shima J, Takagi H (2010) Antioxidant N-acetyltransferase Mpr1/2 of industrial baker's yeast enhances fermentation ability after air-drying stress in bread dough. Int J Food Microbiol 138:181-185
96. Schwartz RE, Giacobbe RA, Bland JA (1989) L-671,329, a new antifungal agent. I. Fermentation and isolation. J Antibiot 42:163-170
97. Sekine T, Kawaguchi A, Hamano Y, Takagi H (2007) Desensitization of feedback inhibition of the yeast γ-glutamyl kinase enhances proline accumulation and freezing tolerance. Appl Environ Microbiol 73:4011-4019
98. Sheehan JC, Mania D, Nakamura S, Stock JA, Maeda K (1968) The structure of telomycin. J Am Chem Soc 90:462-470
99. Shibasaki T, Hashimoto S, Mori H, Ozaki A (2000a) Construction of novel hydroxyproline-producing recombinant Escherichia coli by introducing a proline 4-hydroxylase gene. J Biosci Bioeng 90:522-525
100. Shibasaki T, Mori H, Chiba S, Ozaki A (1999) Microbial proline 4-hydroxylase screening and gene cloning. Appl Environ Microbiol 65:4028-4031
101. Shibasaki T, Mori H, Ozaki A (2000b) Enzymatic production of trans-4-hydroxy-l-proline by regio- and stereospecific hydroxylation of l-proline. Biosci Biotechnol Biochem 64:746-750
102. Shibasaki T, Mori H, Ozaki A (2000c) Cloning of an isozyme of proline 3-hydroxylase and its purification from recombinant Escherichia coli. Biotech Lett 22:1967-1973
103. Shichiri M, Hoshikawa C, Nakamori S, Takagi H (2001) A novel acetyltransferase found in Saccharomyces cerevisiae Σ1278b that detoxifies a proline analogue, azetidine-2-carboxylic acid. J Biol Chem 276:41998-42002
104. Schobert B, Tschesche H (1978) Unusual solution properties of proline and its interaction with proteins. Biochim Biophys Acta 541:270-277
105. Shoulder MD, Kotch FW, Chouhary A, Guzei IA, Raines RT (2010) The aberrance of the 4S diastereomer of 4-hydroxyproline. J Am Chem Soc 132:10857-10865
106. Smirnoff N, Cumbes QJ (1989) Hydroxyl radical scavenging activity of compatible solutes. Phytochemistry 28:1057-1060
107. Sugiura M, Kisumi M (1985) Proline-hyperproducing strains of Serratia marcescens: enhancement of proline analog-mediated growth inhibition by increasing osmotic stress. Appl Environ Microbiol 49:782-786
108. Sung ML, Fowden L (1971) Imino acid biosynthesis in Delonix regia. Phytochemistry 10:1523-1528
109. Takagi H, Iwamoto F, Nakamori S (1997) Isolation of freeze-tolerant laboratory strain of Saccharomyces cerevisiae from proline-analogue-resistant mutants. Appl Microbiol Biotechnol 47:405-411
110. Takagi H, Sakai K, Morida K, Nakamori S (2000a) Proline accumulation by mutation or disruption of the proline oxidase gene improves resistance to freezing and desiccation stresses in Saccharomyces cerevisiae. FEMS Microbiol Lett 184:103-108
111. Takagi H, Shichiri M, Takemura M, Mohri M, Nakamori S (2000b) Saccharomyces cerevisiae Σ1278b has novel genes of the N-acetyltransferase gene superfamily required for l-proline analogue resistance. J Bacteriol 182:4249-4256
112. Takagi H, Takaoka M, Kawaguchi A, Kubo K (2005) Effect of l-proline on sake brewing and ethanol stress in Saccharomyces cerevisiae. Appl Environ Microbiol 71:8656-8662
113. Tan EM, Ryhanen LU (1983) Proline analogues inhibit human skin fibroblast growth and collagen production in culture. J Invest Dermatol 80:261-267
114. Terao Y, Nakamori S, Takagi H (2003) Gene dosage effect of l-proline biosynthetic enzymes on l-proline accumulation and freeze tolerance in Saccharomyces cerevisiae. Appl Environ Microbiol 69:6527-6532
115. Trotter EW, Kao CMF, Berenfeld L, Botstein D, Petsko GA, Gray JV (2002) Misfolded proteins are competent to mediate a subset of the responses to heat shock in Saccharomyces cerevisiae. J Biol Chem 277:44817-44825
116. Tsai FY, Zhang XH, Ulanov A, Widholm JM (2010) The application of the yeast N-acetyltransferase MPR1 gene and the proline analogue l-azetidine-2-carboxylic acid as a selectable marker system for plant transformation. J Exp Bot 61:2561-2573
117. Vetting MW, de Carvalho LP S, Yu M, Hegde SS, Magnet S, Roderick SL, Blanchard JS (2005) Structure and functions of the GNAT superfamily of acetyltransferases. Arch Biochem Biophys 433:212-226
118. Wada M, Okabe K, Kataoka M, Shimizu S, Yokota A, Takagi H (2008) Distribution of l-azetidine-2-carboxylate N-acetyltransferase in yeast. Biosci Biotech Biochem 72:582-586
119. Wantanabe J, Nakad N, Sawairi S, Shimada H, Ohshima S, Kamiyama T, Arisawa M (1994) Cyclothialidine, a novel DNA gyrase inhibitor. I. Screening, taxonomy, fermentation and biological activity. J Antibiot 47:32-38
120. Wieland T (1968) Poisonous principles of mushrooms of the genus Amanita. Four-carbon amines acting on the central nervous system and cell-destroying cyclic peptides are produced. Science 159:946-952
121. 3: a depsipeptide antibiotic active against vancomycin-resistant bacteria. J Am Chem Soc 129:4175-4177
122. Wright NP, Nolan S (2001) N-acetyl-l-hydroxyproline: chromosome aberration test in CHL cells in vitro. SPL project number 732/092. SafePharm Laboratories Ltd., Derby
123. Yeung KF, Lee KM, Woodard RW (1998) Isolation and identification of two l-azetidine-2-carboxylic acid-degrading soil microorganisms, Enterobacter agglomerans and Enterobacter amnigenus. J Nat Prod 61:207-211
124. Yokota S, Yanagi H, Yura T, Kubota H (2000) Upregulation of cytosolic chaperonin CCT subunits during recovery from chemical stress that causes accumulation of unfolded proteins. Eur J Biochem 267:1658-1664
125. Yoshinaga F, Nakamori S (1983) Production of amino acids. In: Herrmann KM, Sommerville RL (eds) Amino acids: biosynthesis and genetic regulation. Addison-Wesley Publishing Company, London, pp 405-429
126. Zhang XH, Takagi H, Widholm JM (2004) Expression of a novel yeast gene that detoxifies the proline analog azetidine-2-carboxylate confers resistance during tobacco seed germination, callus and shoot formation. Plant Cell Rep 22:615-622